期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 23, 页码 9143-9148出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202001824
关键词
ketones; N-heterocyclic carbenes; photochemistry; radicals; reaction mechanisms
资金
- NIGMS NIH HHS [R01 GM073072] Funding Source: Medline
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.
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