Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 49, Pages 17646-17650Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910514
Keywords
alkenes; alkynylation; difunctionalization; monofluoroalkylation; radical reactions
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Funding
- National Natural Science Foundation of China [21722205, 21971173]
- Project of Scientific and Technologic Infrastructure of Suzhou [SZS201708]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
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A radical-mediated monofluoroalkylative alkynylation of alkenes is disclosed for the first time. The reaction demonstrates a remarkably broad substrate scope in which both activated and unactivated alkenes are suitable starting materials. The concurrent addition of an alkynyl and a monofluoroalkyl group onto an alkene proceeds through a docking-migration sequence, affording a vast array of valuable fluoroalkyl-substituted alkynes. Many complex natural products and drug derivatives are readily functionalized, demonstrating that this method can be used for late-stage alkynylation.
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