Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 29, Pages 7629-7633Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201403383
Keywords
aryl migration; copper; radical reactions; Togni's reagent; trifluoromethylation
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Funding
- National Science Foundation [NSF21072081]
- National Basic Research Program of China (973 Program) [2010CB8-33203]
- 111 Project
- Program for Changjiang Scholars and innovative Research Team in University [IRT1138]
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A novel copper-catalyzed one-pot functionalization of homopropargylic alcohols that involves trifluoromethylation, aryl migration, and formation of a carbonyl moiety has been developed. This reaction constitutes the first direct conversion of homopropargylic alcohols into CF3-containing 3-butenal or 3-buten-1-one derivatives in a regioselective manner. Mechanistic studies indicate that the 1,4-aryl migration proceeds through a radical pathway.
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