Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 48, Pages 15847-15851Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809919
Keywords
allylic compounds; nickel; photochemistry; reaction mechanism; synthetic methods
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Funding
- NIGMS [R01 GM 113878]
- NSF [1751568]
- Bristol-Myers Squibb Graduate Fellowship for Synthetic Organic Chemistry
- University of Maryland College Park [CHE160082, CHE160053]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM113878] Funding Source: NIH RePORTER
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A regioselective, nickel-catalyzed photoredox allylation of secondary, benzyl, and alpha-alkoxy radical precursors is disclosed. Through this manifold, a variety of linear allylic alcohols and allylated monosaccharides are accessible in high yields under mild reaction conditions. Quantum mechanical calculations [DET and DLPNO-CCSD(T)/support the mechanistic hypothesis of a Ni-0 to Ni-11 oxidative addition pathway followed by radical addition and inner-sphere allylation.
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