Anti-Markovnikov Hydrofunctionalization of Alkenes

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 [Singapour]
3 Department of Chemistry and Biomolecular Sciences University of Ottawa, D'lorio Hall

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

Domains: Organic chemistry

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, 2017, 56 (38), pp.11440-11444. ⟨10.1002/anie.201705368⟩. ⟨hal-02073907⟩