Anti‐Markovnikov Hydrofunctionalization of Alkenes: Use of a Benzyl Group as a Traceless Redox‐Active Hydrogen Donor

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 derivativ...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-09, Vol.56 (38), p.11440-11444
Main Authors: Lonca, Geoffroy Hervé, Ong, Derek Yiren, Tran, Thi Mai Huong, Tejo, Ciputra, Chiba, Shunsuke, Gagosz, Fabien
Format: Article
Language:English
Subjects:
Alcohols
alkene functionalization
Alkenes
azidation
Catalysis
Chemical Sciences
copper catalysis
Iodine
Organic chemistry
radicals
Reagents
Regioselectivity
trifluoromethylation
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Summary: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. 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201705368