A Co-operative Bimetallic Approach for the Transformation of Lithiation
Lead Research Organisation:
University of Strathclyde
Department Name: Pure and Applied Chemistry
Abstract
Lithiation is one of best tools for building molecules big and small. Its application transcends chemistry and crosses over to other disciplines such as biochemistry and materials science. It offers an efficient direct way of breaking inert C-H bonds (ubiquitous in organic compounds) and transforming them into reactive C-Li bonds which in turn can be used to make a myriad of molecules, that mankind needs to sustain the quality of our daily lives. Organolithium tools find employment in academic laboratories worldwide and in the manufacture of many fine chemicals, in particular pharmaceuticals (it has been estimated that 95% of manufactured pharmaceuticals involve an organolithium tool in their preparation). The best known organolithium tool, butyllithium is near ubiquitous in synthetic chemistry, and its importance continues to escalate as evidenced by the fact that the chemical company FMC recently opened new butyllithium plants in Hyderabad (India) and Zhangjiagang (China) to service the rapidly expanding pharmaceutical business in the emerging BRIC (Brazil-Russia-India-China) economies. Because butyllithium can break numerous carbon-hydrogen bonds as well as performing other bond-breaking, bond-making tasks, it is widely used in drug development. Organolithium tools are also used to prepare other specialty chemicals such as agrochemicals, biochemicals, catalysts, dyes and perfumes.
How to perfect C-H bond activation is one of the World's most pressing scientific grand challenges as new innovative ways must be found for converting cheap and abundant raw materials such as alkanes into precious functionalised organic compounds given the rapid depleting of fossil fuels. Despite its vast utility, lithiation, a direct form of C-H bond activation, suffers from severe limitations. A major limitation which puts a question mark against its long term sustainability is that it is exclusively a stoichiometric process. For example one mole of the organolithium tool is needed to make one mole of the target product. Moreover, lithiation often requires energy wasteful cryogenic conditions as well as ethereal solvents which are expensive and hazardous on a large scale. It also has many intrinsic chemical limitations including a poor tolerance of functional groups, a failure to react with weakly acidic C-H bonds, and incompatibility with subsequent transition metal catalysed bond-forming reactions.
To transform lithiation into a substoichiometric process, ultimately developing it to a catalytic process is the ambitious goal of this project. For example, to use as little as 0.1 mole or less of the organolithium tool to make one mole of the target product. To reach this goal, the project will develop a new concept in bimetallic chemistry, synergistic stepwise metal - metal' co-operativity (basically two metals working one after the other in separate molecules) building on the successful, but wholly distinct foundation of synergic synchronised metal - metal' co-operativity (basically two metals working side-by-side in the same molecule) that the PI has recently pioneered. Initially a lithium-zinc co-operativity will be screened. Developing catalytic lithiation will be groundbreaking with direct chemical and economic benefits as well as indirect societal benefits given the long list of applications mentioned above. A library of interesting, useful new chemistry not currently possible in lithiation will emerge on the journey to achieving catalytic lithiation, including improved methods for direct C-H bond activation, new combined lithiation - Negishi coupling and other combined lithiation - transition metal bond forming strategies, reactions with high functional group tolerance, and "greener" processes using more environmentally friendly solvents and milder reaction conditions. Bonds impossible to break with existing organolithium tools will also be broken using new potassium based tools.
How to perfect C-H bond activation is one of the World's most pressing scientific grand challenges as new innovative ways must be found for converting cheap and abundant raw materials such as alkanes into precious functionalised organic compounds given the rapid depleting of fossil fuels. Despite its vast utility, lithiation, a direct form of C-H bond activation, suffers from severe limitations. A major limitation which puts a question mark against its long term sustainability is that it is exclusively a stoichiometric process. For example one mole of the organolithium tool is needed to make one mole of the target product. Moreover, lithiation often requires energy wasteful cryogenic conditions as well as ethereal solvents which are expensive and hazardous on a large scale. It also has many intrinsic chemical limitations including a poor tolerance of functional groups, a failure to react with weakly acidic C-H bonds, and incompatibility with subsequent transition metal catalysed bond-forming reactions.
To transform lithiation into a substoichiometric process, ultimately developing it to a catalytic process is the ambitious goal of this project. For example, to use as little as 0.1 mole or less of the organolithium tool to make one mole of the target product. To reach this goal, the project will develop a new concept in bimetallic chemistry, synergistic stepwise metal - metal' co-operativity (basically two metals working one after the other in separate molecules) building on the successful, but wholly distinct foundation of synergic synchronised metal - metal' co-operativity (basically two metals working side-by-side in the same molecule) that the PI has recently pioneered. Initially a lithium-zinc co-operativity will be screened. Developing catalytic lithiation will be groundbreaking with direct chemical and economic benefits as well as indirect societal benefits given the long list of applications mentioned above. A library of interesting, useful new chemistry not currently possible in lithiation will emerge on the journey to achieving catalytic lithiation, including improved methods for direct C-H bond activation, new combined lithiation - Negishi coupling and other combined lithiation - transition metal bond forming strategies, reactions with high functional group tolerance, and "greener" processes using more environmentally friendly solvents and milder reaction conditions. Bonds impossible to break with existing organolithium tools will also be broken using new potassium based tools.
Planned Impact
One of the World's most pressing scientific grand challenges is how to perfect C-H bond activation for converting cheap and abundant raw materials such as alkanes into precious functionalised organic compounds given that fossil fuels are expected to significantly diminish in the near future. Lithiation is an extremely efficient existing method of direct C-H activation converting inert C-H bonds into reactive C-Li bonds. Lithiation is practiced worldwide helping to supply the countless number of high quality compounds needed to sustain the quality of human life. For example, remarkably, it has been estimated that 95% of all manufactured pharmaceuticals involve an organolithium reagent in their preparation.
A major limitation of the current state of the art of lithiation, which puts a question mark against its long term sustainability, is that it is invariably a stoichiometric reaction. Developing a substoichiometric process ultimately leading to catalytic lithiation would be a revolutionary breakthrough that would have profound direct benefits for both academia and industry/commerce and indirectly for society in general. A catalogue of novel and useful new chemistry currently impossible in stoichiometric lithiation will emerge on the journey to achieving catalytic lithiation, including improved methods for direct C-H bond activation, new combined lithiation - Negishi coupling and other combined lithiation - transition metal catalysed bond forming strategies, reactions with vastly improved functional group tolerance, and "greener" processes using less toxic solvents and milder reaction conditions.
The project will also impact significantly on the future career prospects of the PDRA. REM has an outstanding track record of mentoring young talent. His international recognition and success as a mentor is reflected by the large number of his ex-researchers who have gone on to successful independent careers in academia/education [e.g., Prof K Henderson (Chair of the Department, University of Notre Dame, USA), Dr PC Andrews (Associate Prof, Monash University, Australia), Dr E Hevia (Reader, University of Strathclyde), Dr CT O'Hara (Senior Lecturer, University of Strathclyde), Dr J Garcia-Alvarez (Ramón y Cajal Fellow, University of Oviedo, Spain), and Dr L Hogg (Programme Manager, Education Division, Royal Society of Chemistry)], or industry [e.g., D Graham (BASF, Germany), Dr B Conway (Johnson-Matthey, UK), and Dr S Weatherstone (E-ON, UK)].
It is essential that research chemists publish their best findings through prestigious interdisciplinary journals (e.g., Nature or Science) where impact is maximised. This represents a great way of reaching a diverse audience of chemists from different specialisations, and other scientists, from across the globe. Reputations and marketability (for example, in potential to attract future grant income and industrial support) can soar as a result of having published papers in such prestige forums. In this project key results will also be published in world-leading general chemistry journals (e.g., Angewandte Chemie; Journal of the American Chemical Society; Nature Chemistry; but also Chemical Communications; Chemistry-A European Journal).
The University of Strathclyde/WestCHEM has a good track record in collaborating with industry and commercialising its innovations through patent protection and spin-off companies. While the basic science in this project will not be immediately marketable it is anticipated that progress towards achieving substoichiometric or catalytic lithiation will appeal to pharmaceutical companies in particular. REM will therefore use his new PhD studentship collaboration with AstraZeneca UK (industrial supervisor, Phil O'Keefe) for knowledge transfer discussions on the possibility of adapting the basic Schlenk bench-top chemistry of the project to a larger process scale for industrial utilisation.
A major limitation of the current state of the art of lithiation, which puts a question mark against its long term sustainability, is that it is invariably a stoichiometric reaction. Developing a substoichiometric process ultimately leading to catalytic lithiation would be a revolutionary breakthrough that would have profound direct benefits for both academia and industry/commerce and indirectly for society in general. A catalogue of novel and useful new chemistry currently impossible in stoichiometric lithiation will emerge on the journey to achieving catalytic lithiation, including improved methods for direct C-H bond activation, new combined lithiation - Negishi coupling and other combined lithiation - transition metal catalysed bond forming strategies, reactions with vastly improved functional group tolerance, and "greener" processes using less toxic solvents and milder reaction conditions.
The project will also impact significantly on the future career prospects of the PDRA. REM has an outstanding track record of mentoring young talent. His international recognition and success as a mentor is reflected by the large number of his ex-researchers who have gone on to successful independent careers in academia/education [e.g., Prof K Henderson (Chair of the Department, University of Notre Dame, USA), Dr PC Andrews (Associate Prof, Monash University, Australia), Dr E Hevia (Reader, University of Strathclyde), Dr CT O'Hara (Senior Lecturer, University of Strathclyde), Dr J Garcia-Alvarez (Ramón y Cajal Fellow, University of Oviedo, Spain), and Dr L Hogg (Programme Manager, Education Division, Royal Society of Chemistry)], or industry [e.g., D Graham (BASF, Germany), Dr B Conway (Johnson-Matthey, UK), and Dr S Weatherstone (E-ON, UK)].
It is essential that research chemists publish their best findings through prestigious interdisciplinary journals (e.g., Nature or Science) where impact is maximised. This represents a great way of reaching a diverse audience of chemists from different specialisations, and other scientists, from across the globe. Reputations and marketability (for example, in potential to attract future grant income and industrial support) can soar as a result of having published papers in such prestige forums. In this project key results will also be published in world-leading general chemistry journals (e.g., Angewandte Chemie; Journal of the American Chemical Society; Nature Chemistry; but also Chemical Communications; Chemistry-A European Journal).
The University of Strathclyde/WestCHEM has a good track record in collaborating with industry and commercialising its innovations through patent protection and spin-off companies. While the basic science in this project will not be immediately marketable it is anticipated that progress towards achieving substoichiometric or catalytic lithiation will appeal to pharmaceutical companies in particular. REM will therefore use his new PhD studentship collaboration with AstraZeneca UK (industrial supervisor, Phil O'Keefe) for knowledge transfer discussions on the possibility of adapting the basic Schlenk bench-top chemistry of the project to a larger process scale for industrial utilisation.
Organisations
Publications
Armstrong D
(2014)
TMP (2,2,6,6-tetramethylpiperidide)-aluminate bases: lithium-mediated alumination or lithiation-alkylaluminium-trapping reagents?
in Chem. Sci.
Armstrong D
(2013)
Modifying Alkylzinc Reactivity with 2,2'-Dipyridylamide: Activation of t Bu?Zn Bonds for para -Alkylation of Benzophenone
in Angewandte Chemie
Armstrong DR
(2014)
Donor-activated alkali metal dipyridylamides: co-complexation reactions with zinc alkyls and reactivity studies with benzophenone.
in Dalton transactions (Cambridge, England : 2003)
Armstrong DR
(2015)
Developing lithium chemistry of 1,2-dihydropyridines: from kinetic intermediates to isolable characterized compounds.
in Chemistry (Weinheim an der Bergstrasse, Germany)
Armstrong DR
(2013)
Modifying alkylzinc reactivity with 2,2'-dipyridylamide: activation of tBu-Zn bonds for para-alkylation of benzophenone.
in Angewandte Chemie (International ed. in English)
Benhamou L
(2016)
Synthesis of substituted benzooxaborinin-1-ols via palladium-catalysed cyclisation of alkenyl- and alkynyl-boronic acids.
in Organic & biomolecular chemistry
Brouillet EV
(2016)
Exposing elusive cationic magnesium-chloro aggregates in aluminate complexes through donor control.
in Dalton transactions (Cambridge, England : 2003)
Clegg W
(2015)
Structurally Defined Zincated and Aluminated Complexes of Ferrocene Made by Alkali-Metal Synergistic Syntheses
in Organometallics
Coomber CE
(2018)
Silver-Free Palladium-Catalyzed C(sp3)-H Arylation of Saturated Bicyclic Amine Scaffolds.
in The Journal of organic chemistry
Fuentes MÁ
(2016)
Revealing the remarkable structural diversity of the alkali metal transfer agents of the trans-calix[2]benzene[2]pyrrolide ligand.
in Chemical communications (Cambridge, England)
| Description | The challenge behind this project was to upgrade lithiation (Li-H exchange reactions) and metallation (metal-hydrogen exchange reactions) in general. Though metallation has served the synthetic community for several decades as a key vehicle towards the synthesis and manufacture of agrochemicals, biosynthetic chemicals, functional materials, pharmaceuticals and many other commodity fine chemicals, it is severely limited by low functional group tolerance, the instability of metallated intermediates, the need for subambient temperatures and the lack of any catalytic regime. The last challenge represents the grandest of them all. Towards finding a catalytic regime we developed a cycle in which a lithium amide (e.g., lithium 2,2,6,6-tetramethylpiperidide, LiTMP) would deprotonate an organic substrate, for example a substituted aromatic compound, then intercept this with a zinc amide or aluminum amide of the same amide anion (e.g., TMP) so that a new, more stable, C-Zn or C-Al bond would form and at the same time regenerate the original lithium amide to close the cycle. Though the initial lithiations were successful, and the subsequent transmetallation produced the target Zn-C or Al-C bonds, the interception reaction produced bimetallic (e.g., Li-Zn or Li-Al) ates that stopped the recycling of the lithium reagent. We traced this stoppage to the coordinatively saturated nature of the ate, that is, they would not eliminate LiTMP. Subsequently, we exploited this seemingly problematic ate coordinative saturation in an exciting new concept of "trans-metal-trapping". Thus, carrying out lithiations of challenging weakly acidic substrates such as anisoles via LiTMP that produced poor yields of the desired lithiated products but introducing an aluminium trapping agent, for example a bisalkyl-amide, we not only stabilised sensitive metallated intermediates but remarkably could shift reaction equilibria such that desired products could be obtained in quantitative yield. Published in the high impact journal Chemical Science (2014, 5, 3031), this breakthrough suggests that refinement of trans-metal-trapping could potentially transform any failed lithiation reaction into a successful lithiation reaction, thus achieving one of the main goals of the project. We demonstrated this in our next study. Conventional lithiation of benzotriazole, an important heterocycle in numerous material and biochemical applications, via monometallic LiTMP produced an unclean reaction in which ring opening and N2 extrusion of the heterocycle took place. However, attempting the same reaction with the bimetallic trans-metal-trapping approach led to much cleaner reactions and high yields of the desired aluminated benzotriazoles. Another part of the project established that donor-activated alkali metal dipyridylamides could activate zinc alkyl reagents towards alkylation of aromatic ketones. In the best cases, the nucleophilic addition occurred at the para position of the aromatic ring, in a highly unusual regioselective process. On their own, the zinc alkyls are inert, thus showing that a bimetallic synergic reactivity is operating in these reactions. The fact that the alkali metal component of the synergic partnership could function under substoichiometric conditions, suggests that it should be possible with further work to make these reactions catalytic. Overall the project has contributed significantly to the development of synergistic reactivity in polar organometallic chemistry. |
| Exploitation Route | Results from this project will be used as the basis for other grant applications at EPSRC, EU and industry. The new methodologies described could potentially be exploited by other synthetic chemists. |
| Sectors | Chemicals |
| Description | This project was conceived on two big vision ideas. (i) That the chemistry of the alkali metal lithium used stoichiometrically in synthetic chemistry for a century could be developed to start making an impact in catalysis as an alternative to the expensive, environmentally harmful, low earth abundant precious transition metals. This is important as catalysis is fundamental to the development of sustainable processes enabling innovative, efficient routes to chemicals essential for humankind, which is why more than 90% of industrial chemical processes use catalysts. (ii) That one way to achieve this ambitious objective was to design bimetallic compounds containing lithium and another metal such as zinc that would exhibit chemical reactivity beyond that of single metal compounds through the switching on of metal-metal cooperativities or synergistic effects. Substantial progress towards both of these objectives were made in the project through the publication of nine academic papers. Since this project was initiated in 2013, there has been a growing body of work including that in the project papers which have propelled these ideas to the forefront of the emerging area of main group catalysis. Two recent articles in chemical reviews (impact factor, 60.62), one from our group "Alkali-Metal-Mediated Synergistic Effects in Polar Main Group Organometallic Chemistry (2019, 119, 8332)" and one from Hill/Aldridge, "Molecular Main Group Metal Hydrides (2021, 121, 12784) and a book by Harder "Early Main Group Metal Catalysis, Wiley-VCH, 2020" underline this emerging field of research. The field is still in its nascent phase and industry has still to embrace it to any significant extent, but it has a growing momentum about it which is why funding bodies such as the EPSRC should support its development given its vast scope for future applications in industries that employ homogeneous catalysts. Tangible impacts from the project include helping the researcher resource in Europe by providing it with two well trained, highly skilled researchers, both of whom have progressed to important research roles, one in Spain (in academia) and the other in Germany (in a large multinational industrial company). This benefits the economies of these countries and enhances the international profile and reputation of the UK. Another beneficiary was the PhD student associated with the project who was internally funded by the University. This student took advantage of the knowledge and expertise gained from the project to a subsequent postdoctoral position in a Russell University and cleverly applied the idea of bimetallic cooperativity to sustainable polymerisation chemistry that utilises the greenhouse gas CO2 as a feedstock. This work sponsored by industry was patented. This ex-student has now got a fully independent tenured position at another Russell University and has a substantial funding profile. Our own work on lithium has received follow-up funding to develop the chemistry of its nearest group one neighbour sodium, which is even more important from a sustainability viewpoint as it is the most abundant alkali metal in the earth's crust and in the oceans. The project is entitled "Propelling Sodium to the Forefront of Metallation Chemistry" and is funded by the Leverhulme Trust (award, £250,408). |
| Impact Types | Economic |
| Description | Propelling Sodium to the Forefront of Metallation Chemistry |
| Amount | £250,408 (GBP) |
| Funding ID | RPG-2019-264 |
| Organisation | The Leverhulme Trust |
| Sector | Charity/Non Profit |
| Country | United Kingdom |
| Start | 08/2020 |
| End | 03/2024 |
| Title | Revealing the remarkable structural diversity of the alkali metal transfer agents of the trans-calix[2]benzene[2]pyrrolidide ligand |
| Description | The data set contains four files. These data relate to the research discussed in the manuscript "Revealing the remarkable structural diversity of the alkali metal transfer agents of the trans-calix[2]benzene[2]pyrrolidide ligand". Corresponding authors: M. Ángeles Fuentes, Antonio J. Martínez-Martínez, Alan R. Kennedy and Robert E. Mulvey*. This work was made possible through generous financial support from the EPSRC for the project "A co-operative bimetallic approach for the transformation of lithiation" (award no. EP/K001183/1) and the Royal Society (Wolfson research merit award to R.E.M). PI: Professor R. E. Mulvey; PDRA: Dr M. Á. Fuentes. This manuscript advances alkali metal chemistry of the trans-calix[2]benzene[2]pyrrolidide ligand showing a remarkable structural diversity. These novel complexes can be consider very important as alkali metal ligand transfer agents for organoactinide and organolanthaide chemistry. All complexes have been characterized by X-ray crystallography, NMR spectroscopy and elemental analysis. Files present: 1. General procedures 2. NMR spectroscopy and elemental analysis 3. X-Ray crystallographic structures 4. CIF for the crystallographic structures Please, note that to view the cif files it is necessary to use a graphical program which can open crystallography files (programs such as Mercury, ORTEP-3, etc). |
| Type Of Material | Database/Collection of data |
| Year Produced | 2016 |
| Provided To Others? | Yes |
| Impact | n/a |
| Title | Structural Studies of the Deprotometalation and Trans-Metal-Trapping Chemistry of a Substituted Benzotriazole |
| Description | "The data set contains three files. These data relate to the research discussed in the manuscript, "Adding a Structural Context to the Deprotometalation and Trans-Metal-Trapping Chemistry of Phenyl-substituted Benzotriazole" which has been published in Chem. Eur. J. 2015, 21, 14812 - 14822. The work was carried out in relation to the EPSRC grant, "A co-operative bimetallic approach for the transformation of lithiation". EP/K001183/1. PI: Professor R E Mulvey; PDRA: Dr M. Angeles Fuentes. Organometallic bases are considered one of the most important synthetic tools for the regio-, chemo- and enantio-selective functionalisation of aromatic compounds. Mixing organometallic reagents can lead to superior bases giving different chemistry from to single-component bases. Previous work within the Mulvey research group has shown that lithium amide LiTMP (TMP = 2,2,6,6-tetramethylpiperidide) does not co-complex with bulky alkyl-TMP-aluminium reagents, instead LiTMP will deprotonate a substrate while the aluminium moiety can function as an effective trans-metal trapping agent. For example, anisole can be metallated by LiTMP in a very low yield (?5%) but in the presence of trapping agent iBu2Al(TMP) this C-H deprotonation becomes near quantitative.1 The benzotriazole ring is a heterocyclic scaffold present in many important synthetic and bioactive molecules. One of the challenges in this area is to bring about the regioselective functionalization of 1-phenyl-1H-benzotriazole, 1, which was previously deprotonated by an in situ ZnCl2·TMEDA/LiTMP (TMEDA = N,N,N',N'-tetramethylethylenediamine) mixture and then iodinated.2 No information on intermediates was obtained from this in situ quenching approach. We have studied this molecule with different organometallic bases and attempted to gain insight into the metallo intermediates involved. Contrasting results have been obtained using the harsh base LiTMP on its own or in the more interesting LiTMP/iBu2Al(TMP) trapping protocol. All the complexes in this project can undergo quenching with electrophiles giving high value compounds potentially of significance for the fine chemicals industry. Files present: 1. General procedures and synthesis.pdf 2. NMR spectroscopy and elemental analysis.pdf 3. X-Ray crystallographic structures.pdf References 1. D.R. Armstrong, E. Crosbie, E. Hevia, R.E. Mulvey, D.L. Ramsay and S.D. Robertson, Chem. Sci. 2014, 5, 3031. 2. E. Nagaradja, F. Chevallier, T. Roisnel, V. Dorcet, Y.S. Halauko, O.A. Ivashkevich, V.E. Matulis and F. Mongin, Org. Biomol. Chem. 2014, 12, 1475." |
| Type Of Material | Database/Collection of data |
| Provided To Others? | No |
| Impact | Not recorded |
| Title | Structural diversity in alkali metal and alkali metal magnesiate chemistry of the bulky 2,6-diisopropyl-N-(trimethylsilyl)anilino ligand |
| Description | Organometallic bases are considered one of the most important synthetic tools for the regio-, chemo- and enantio-selective functionalisation of organic molecules. In this research we have attempted to expand the scope of bimetallic bases by employing a previously little studied bulky amide. Within this work a novel series of homometallic and heterobimetallic complexes have been synthesised and characterized by X-ray crystallography and NMR spectroscopy. This research advances alkali metal and alkali metal magnesiate chemistry of the bulky aryl-silyl amido ligand N(SiMe3)(Dipp)] (Dipp = 2,6-iPr2-C6H3). It shows that chain structures as opposed to ring structures will be generally preferred when the bulky amide carries aromatic groups which can engage through their pi systems to alkali metals. Thus template ring bases cannot be made with this particular amide. The data set contains four files: 1. General procedures 2. NMR spectroscopy and elemental analysis 3. X-Ray crystallographic structures 4. CIF for the crystallographic structures Please, note that to see the cif files requires a graphical program which can open crystallographic files (programs such as Mercury, ORTEP-3, etc.). This work was generously supported by the UK Engineering and Physical Science Research Council (award no. EP/K001183/1) and the Royal Society (Wolfson research merit award to R.E.M). PI: Professor R. E. Mulvey; PDRA: Dr M. Á. Fuentes. |
| Type Of Material | Database/Collection of data |
| Year Produced | 2016 |
| Provided To Others? | Yes |
| Impact | n/a |
| Description | Alkali metal mediation in synergistic synthesis and catalysis |
| Form Of Engagement Activity | A talk or presentation |
| Part Of Official Scheme? | No |
| Geographic Reach | National |
| Primary Audience | Professional Practitioners |
| Results and Impact | Invited lecture at University of Sheffield |
| Year(s) Of Engagement Activity | 2017 |
| Description | Invited Seminar University of Oxford: Pre-organised base approaches to metallation chemistry |
| Form Of Engagement Activity | A talk or presentation |
| Part Of Official Scheme? | No |
| Geographic Reach | National |
| Primary Audience | Other audiences |
| Results and Impact | Invited Seminar University of Oxford: Pre-organised base approaches to metallation chemistry. This presentation facilitated the sharing of information with other academic audiences (collaborators, peers etc.). |
| Year(s) Of Engagement Activity | 2016 |
| Description | M. Fuentes: C-H bond functionalization of 1-phenyl-1H-benzotriazole: Aluminations and illuminations" Dalton Division Poster Symposium. London, UK |
| Form Of Engagement Activity | A talk or presentation |
| Part Of Official Scheme? | No |
| Geographic Reach | National |
| Primary Audience | Postgraduate students |
| Results and Impact | Great meeting at the RSC Burlington House where I networked with postgraduate peers from all over the UK. |
| Year(s) Of Engagement Activity | 2015 |
| Description | M. Fuentes: Poster Presentation: International Chemical Congress of Pacific Basin Societies (Pacifichem). Book of abstracts, P-1947. Honolulu, (Hawaii), USA |
| Form Of Engagement Activity | A talk or presentation |
| Part Of Official Scheme? | No |
| Geographic Reach | International |
| Primary Audience | Professional Practitioners |
| Results and Impact | My poster presentation received lots of interest from delegates. I had a number of informative discussions with both peers and senior academics that inspired me to try new chemistry on my return to Strathclyde university. |
| Year(s) Of Engagement Activity | 2015 |