期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 10, 页码 3132-3135出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201411657
关键词
alkyl nitriles; allylic alcohols; copper triflate; ketones; neophyl rearrangement
资金
- EPFL (Switzerland)
- Swiss National Science Foundation (SNSF)
A copper-catalyzed alkylation of allylic alcohols by alkyl nitriles with concomitant 1,2-aryl migration was developed. Formation of the alkyl nitrile radical was followed by its intermolecular addition to alkenes and the migration of a vicinal aryl group with the concomitant generation of a carbonyl functionality to complete the domino sequence. Mechanistic studies suggested that 1,2-aryl migration proceeded through a radical pathway (neophyl rearrangement). The protocol provided an efficient route to functionalized ketones containing an -quaternary center.
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