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

Autor: Lonca GH; Département de Chimie, UMR 7652 and 7653 CNRS, Ecole Polytechnique, 91128, Palaiseau, France., Ong DY; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore., Tran TMH; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore., Tejo C; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore., Chiba S; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore., Gagosz F; Département de Chimie, UMR 7652 and 7653 CNRS, Ecole Polytechnique, 91128, Palaiseau, France.; Department of Chemistry and Biomolecular Sciences, University of Ottawa, K1N 6N5, Ottawa, Canada.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2017 Sep 11; Vol. 56 (38), pp. 11440-11444. Date of Electronic Publication: 2017 Aug 09.
DOI: 10.1002/anie.201705368
Abstrakt: 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 CF 3 - or N 3 -containing hypervalent iodine reagents, a series of homoallylic alcohol derivatives were hydrofunctionalized regioselectivity. A similar principle was also applied to the hydrofunctionalization of alkenols.
(© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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