Tandem Iron Catalysis: A General One-Pot Multistep Synthesis of Heterocycles
Lead Research Organisation:
University of Glasgow
Department Name: School of Chemistry
Abstract
The key aim of this project is to develop one-pot multi-step reactions involving sustainable catalysts such as iron and copper. In particular, we will develop tandem catalytic reactions where an iron complex will be used to catalyse multiple steps, allowing the general synthesis of aryl C-N, C-O, C-S and C-C bonds. Extension of this process using an internal aryl nucleophile and further iron catalysis will allow rapid access to a wide range of highly functionalised heterocycles, synthetic building blocks and intermediates for green and pot efficient preparation of biologically and medicinally important targets as well as heterocyclic compounds for materials science.
Organisations
People |
ORCID iD |
| Andrew Sutherland (Primary Supervisor) | |
| Martyn Henry (Student) |
Studentship Projects
| Project Reference | Relationship | Related To | Start | End | Student Name |
|---|---|---|---|---|---|
| EP/N509668/1 | 01/10/2016 | 30/09/2021 | |||
| 1791216 | Studentship | EP/N509668/1 | 03/10/2016 | 31/03/2020 | Martyn Henry |
| Description | My work on developing one-pot iron catalysed reactions for the preparation of biologically active compounds has already led to a series of papers (J. Org. Chem., 2017, 82, 7529; Synthesis, 2017, 49, 4586). In addition to this, I've completed and published a major project that reports a sequential iron and copper catalysed heterocyclisation reaction for the synthesis of medicinally important heterocycles including the total synthesis of (+)-obtusafuran. (J. Org. Chem., 2019, 84, 346). I'm also developing a method of selective ortho-C-H amination of aromatic compounds without the need for an auxilliary directing group. This versatility and synthetic utility of this methodology was demonstrated with the late-stage functionalisation of dihydroquinolinones to synthesise biologically active protein inhibitors. This work was published in OBC (Org. Biomol. Chem., 2019, 17, 4269). The one-pot iron(III) and copper(I)-catalysed one-pot process was expanded to cover the synthesis of other functional heterocycles such as benzofurans, benzoxazoles and benzothiazoles. Pharmaceutically relevant heterocycles were prepared using this method including compounds with the potential activity against Duchenne muscular dystrophy and Alzheimer's disease. This methodology was also used in the total synthesis of benzo[b]furan natural products corsifuran C, moracin F and caleprunin B. |
| Exploitation Route | I've already shown that the methodology I've been developing during my PhD has already been used to prepare medicinally relevant molecules. It is hoped that it could be used by others to prepare important, biologically active compounds in a rapid and selective manner from simple, readily available starting materials. |
| Sectors | Agriculture, Food and Drink,Chemicals,Pharmaceuticals and Medical Biotechnology |