Abstract
As a key element in the construction of complex organic scaffolds, the formation of C−C bonds remains a challenge in the field of synthetic organic chemistry. Recent advancements in single-electron chemistry have enabled new methods for the formation of various C−C bonds. Disclosed herein is the development of a novel single-electron reduction of acyl azoliums for the formation of ketones from carboxylic acids. Facile construction of the acyl azolium in situ followed by a radical–radical coupling was made possible merging N-heterocyclic carbene (NHC) and photoredox catalysis. The utility of this protocol in synthesis was showcased in the late-stage functionalization of a variety of pharmaceutical compounds. Preliminary investigations using chiral NHCs demonstrate that enantioselectivity can be achieved, showcasing the advantages of this protocol over alternative methodologies.
Original language | English (US) |
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Pages (from-to) | 9143-9148 |
Number of pages | 6 |
Journal | Angewandte Chemie - International Edition |
Volume | 59 |
Issue number | 23 |
DOIs | |
State | Published - Jun 2 2020 |
Keywords
- N-heterocyclic carbenes
- ketones
- photochemistry
- radicals
- reaction mechanisms
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)