Anti-Markovnikov Hydrofunctionalization of Alkenes

Geoffroy Hervé Lonca; Derek Yiren Ong; Thi Mai Huong Tran; Ciputra Tejo; Shunsuke Chiba; Fabien Gagosz

doi:10.1002/anie.201705368

Journal articles

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

Document type :

Journal articles

Domain :

Chemical Sciences / Organic chemistry

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https://hal-polytechnique.archives-ouvertes.fr/hal-02073907
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Submitted on : Wednesday, March 20, 2019 - 12:19:29 PM
Last modification on : Friday, April 12, 2019 - 1:31:46 AM

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

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

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