期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 14, 页码 5003-5006出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b01373
关键词
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资金
- National Institute of General Medical Sciences [R35GM119652]
- Stony Brook University
- NIH [T32GM092714]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1358959] Funding Source: National Science Foundation
Umpolung (polarity reversal) strategies of aldehydes and imines have dramatically expanded the scope of carbonyl and iminyl chemistry by facilitating reactions with non-nucleophilic reagents. Herein, we report the first visible light photoredox-catalyzed beta-selective reductive coupling of alkenylpyridines with carbonyl or iminyl derivatives with the aid of a Lewis acid co-catalyst. Our process tolerates complex molecular scaffolds (e.g., sugar, natural product, and peptide derivatives) and is applicable to the preparation of compounds containing a broad range of heterocyclic moieties. Mechanistic investigations indicate that the key step involves single-electron-transfer reduction of aldehydes or imines followed by the addition of resulting ketyl or alpha-aminoalkyl radicals to Lewis acid-activated alkenylpyridines.
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