Anti‐Markovnikov Hydrofunctionalization of Alkenes: Use of a Benzyl Group as a Traceless Redox‐Active Hydrogen Donor. Issue 38 (9th August 2017)

• Record Type: Journal Article
• Authors: Lonca, Geoffroy Hervé; Ong, Derek Yiren; Tran, Thi Mai Huong; Tejo, Ciputra; Chiba, Shunsuke; Gagosz, Fabien
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 38(2017)
• Page Start: 11440
• Page End: 11444
• Publication Date: 2017-08-09
• Subjects: alkene functionalization -- azidation -- copper catalysis -- radicals -- trifluoromethylation; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201705368
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A protocol for the anti‐Markovnikov hydrofunctionalization of alkenes has been developed by the use of a benzyl group as a traceless redox‐active hydrogen donor. Under copper catalysis and in the presence of CF3 ‐ or N3 ‐containing hypervalent iodine reagents, a series of homoallylic alcohol derivatives were hydrofunctionalized regioselectivity. A similar principle was also applied to the hydrofunctionalization of alkenols. Abstract : A retiring donor : A procedure was developed for the anti‐Markovnikov hydrofunctionalization of alkenes by the use of a benzyl group as a traceless redox‐active hydrogen donor (see scheme). Under copper catalysis in the presence of CF3 ‐ or N3 ‐containing hypervalent iodine reagents, a series of homoallylic alcohol derivatives underwent regioselective hydrofunctionalization. A similar principle was applied to the hydrofunctionalization of alkenols.