期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 52, 页码 17156-17160出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201811346
关键词
alkene difunctionalization; difluoromethylation; heteroarylation; migration; radical reactions
资金
- National Natural Science Foundation of China [21722205]
- Project of Scientific and Technologic Infrastructure of Suzhou [SZS201708]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
Radical-mediated difunctionalization of alkenes is a powerful tactic for olefin utilization. However, the transformation of unactivated alkenes still remains a formidable challenge. Now a conceptually new docking-migration strategy is presented for the difunctionalization of alkenes with photo-redox catalysis. Both activated and unactivated alkenes are suitable substrates. A vast array of functional groups are compatible with the mild reaction conditions. Heteroaryl and difluoromethyl are concomitantly incorporated into alkenes, leading to synthetically valuable products that are readily converted into a variety of fluorine-containing molecules. The protocol provides a kinetic control of stereoselectivity for cycloalkenes to generate the unusual cis-products, and offers an efficient approach for the late-stage functionalization of complex natural products and drug molecules. A portfolio of dual-function reagents are prepared for the elusive radical difunctionalization of alkenes.
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