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

Geoffroy Hervé Lonca 1 Derek Yiren Ong 2 Thi Mai Huong Tran 2 Ciputra Tejo 2 Shunsuke Chiba 2 Fabien Gagosz 1, 3
1 DCSO - Laboratoire de synthèse organique
2 Nanyang Technological University, School of Physical and Mathematical Sciences, Division of Chemistry and Biological Chemistry
3 Department of Chemistry and Biomolecular Sciences University of Ottawa, D'lorio Hall
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.
Keywords : alkene functionalization azidation copper catalysis radicals trifluoromethylation
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Journal articles
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https://hal-polytechnique.archives-ouvertes.fr/hal-02073907
Contributor : Aurélien Arnoux <>
Submitted on : Wednesday, March 20, 2019 - 12:19:29 PM
Last modification on : Friday, April 12, 2019 - 1:31:46 AM

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Geoffroy Hervé Lonca, Derek Yiren Ong, Thi Mai Huong Tran, Ciputra Tejo, Shunsuke Chiba, et al.. Anti-Markovnikov Hydrofunctionalization of Alkenes: Use of a Benzyl Group as a Traceless Redox-Active Hydrogen Donor. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2017, 56 (38), pp.11440-11444. ⟨10.1002/anie.201705368⟩. ⟨hal-02073907⟩

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