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Efficient Docking–Migration Strategy for Selective Radical Difluoromethylation of Alkenes.
- Source :
-
Angewandte Chemie International Edition . Dec2018, Vol. 57 Issue 52, p17156-17160. 5p. - Publication Year :
- 2018
-
Abstract
- 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 photoredox 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. All aboard: A conceptually new docking–migration strategy for the difunctionalization of alkenes under visible‐light photoredox catalysis is disclosed. Both activated and unactivated alkenes are suitable substrates. A vast array of functional groups are compatible with the mild reaction conditions. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ALKENES
*DIFLUOROMETHYL compounds
*STEREOSELECTIVE reactions
*FLUORINE
*HALOGENS
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 57
- Issue :
- 52
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 133626486
- Full Text :
- https://doi.org/10.1002/anie.201811346