Photocatalysis for Organic Synthesis
Lead Research Organisation:
University of St Andrews
Department Name: Chemistry
Abstract
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People |
ORCID iD |
| John Walton (Principal Investigator) |
Publications
Manley DW
(2014)
Catalyst-free photoredox addition-cyclisations: exploitation of natural synergy between aryl acetic acids and maleimide.
in Chemistry (Weinheim an der Bergstrasse, Germany)
Manley DW
(2014)
A clean and selective radical homocoupling employing carboxylic acids with titania photoredox catalysis.
in Organic letters
Manley DW
(2014)
Titania-promoted carboxylic acid alkylations of alkenes and cascade addition-cyclizations.
in The Journal of organic chemistry
Manley DW
(2012)
Unconventional titania photocatalysis: direct deployment of carboxylic acids in alkylations and annulations.
in Journal of the American Chemical Society
Manley DW
(2015)
Preparative semiconductor photoredox catalysis: An emerging theme in organic synthesis.
in Beilstein journal of organic chemistry
Manley DW
(2014)
Hydrogenations without hydrogen: titania photocatalyzed reductions of maleimides and aldehydes.
in Molecules (Basel, Switzerland)
McBurney R
(2012)
Microwave assisted radical organic syntheses
in RSC Adv.
McBurney R
(2013)
Rapid and selective spiro-cyclisations of O-centred radicals onto aromatic acceptors
in Chemical Science
McBurney R
(2012)
An all-purpose preparation of oxime carbonates and resultant insights into the chemistry of alkoxycarbonyloxyl radicals
in Chemical Science
McBurney RT
(2011)
UV promoted phenanthridine syntheses from oxime carbonate derived iminyl radicals.
in Chemical communications (Cambridge, England)
| Description | Our new unconventional titania photocalyses work with with unprocessed carboxylic acids. As a heterogeneous catalyst titania is cheap, easily separated by filtration and safe; no hard UV is needed. The carboxylic acids can be used directly without any special functionalization so the syntheses are very user-friendly. In exploring this chemistry we uncovered several interesting and intriguing aspects. Used without a reaction partner, carboxylic acids decarboxylated and then selectively produced high yields of homo-dimeric products. Alkoxymethyl and aryloxymethyl radicals were generated particularly efficiently. We successfully deployed them in convenient alkylations of electron-deficient alkenes. We also discovered a remarkable cascade reaction in which phenoxyacetic acid reacts with maleic anhydride or a maleimide to yield chromenedione derivatives. Furthermore, by judicious modifications of the catalyst and reaction conditions, this process could be directed either to yield the chromenediones or to produce the alkylated alkenes. In short, we showed that our "clean" anaerobic TiO2-based method has great potential for original syntheses and for making many of the molecules usually associated with toxic organotin methodology. |
| Exploitation Route | As an environmentally friendly way of making biologically active compounds |
| Sectors | Agriculture, Food and Drink,Chemicals,Healthcare,Pharmaceuticals and Medical Biotechnology |
| Description | In the development of a large scale reactor for preparing fine chemicals. |
| First Year Of Impact | 2014 |
| Sector | Chemicals,Pharmaceuticals and Medical Biotechnology |
| Impact Types | Societal,Economic |
| Title | Novel organic reactor for organic synthesis |
| Description | New reactor designed, built and tested. |
| Type Of Material | Improvements to research infrastructure |
| Year Produced | 2015 |
| Provided To Others? | Yes |
| Impact | not yet known |
| Description | Photocatalysis for organic synthesis |
| Organisation | Queen's University Belfast |
| Country | United Kingdom |
| Sector | Academic/University |
| PI Contribution | Development of photo-catalysed syntheses |
| Collaborator Contribution | Spectroscopy |
| Impact | See publications in portfolio |
| Start Year | 2011 |
| Description | Photocatalysis for organic synthesis |
| Organisation | University of Aberdeen |
| Country | United Kingdom |
| Sector | Academic/University |
| PI Contribution | Development of photo-catalysed syntheses |
| Collaborator Contribution | Spectroscopy |
| Impact | See publications in portfolio |
| Start Year | 2011 |
| Description | 5th Pacific symposium on radical chemistry, Japan |
| Form Of Engagement Activity | A talk or presentation |
| Part Of Official Scheme? | No |
| Geographic Reach | International |
| Primary Audience | Professional Practitioners |
| Results and Impact | Presented a poster. Engaged in discussions. |
| Year(s) Of Engagement Activity | 2007,2011 |
| Description | Pacific symposium on radical chemistry |
| Form Of Engagement Activity | A talk or presentation |
| Part Of Official Scheme? | No |
| Geographic Reach | International |
| Primary Audience | Professional Practitioners |
| Results and Impact | Displayed poster on project research. Engaged with many who read it. |
| Year(s) Of Engagement Activity | 2013 |
| Description | Royal Soc. Chem. Scottish Regional Meeting |
| Form Of Engagement Activity | A talk or presentation |
| Part Of Official Scheme? | No |
| Geographic Reach | Regional |
| Primary Audience | Professional Practitioners |
| Results and Impact | Presented poster and engaged in discussions. Much interest expressed. |
| Year(s) Of Engagement Activity | 2011,2012 |
| Description | US National Chemistry Conference |
| Form Of Engagement Activity | A talk or presentation |
| Part Of Official Scheme? | No |
| Geographic Reach | International |
| Primary Audience | Professional Practitioners |
| Results and Impact | Displayed a poster of research and engaged verbally with a good number of the > 500 who attended. Interest was expressed and contacts were made. |
| Year(s) Of Engagement Activity | 2013 |
| Description | gordon research conference on heterocyclic compounds, USA |
| Form Of Engagement Activity | A talk or presentation |
| Part Of Official Scheme? | No |
| Geographic Reach | International |
| Primary Audience | Professional Practitioners |
| Results and Impact | Presented a poster. Engaged in discussions with participants. Made contacts. |
| Year(s) Of Engagement Activity | 2012 |