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Radical-Mediated Alkenylation, Alkynylation, Methanimination, and Cyanation of B-Alkylcatecholboranes

Arnaud-Pierre Schaffner, Vincent Darmency, Philippe Renaud*

*Universität Bern, Departement für Chemie und Biochemie, Freiestrasse 3, 3000 Bern 9, Switzerland, Email:

A.-P. Schaffner, V. Darmency, P. Renaud, Angew. Chem. Int. Ed., 2006, 45, 5847-5849.

DOI: 10.1002/anie.200601206 (free Supporting Information)

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Hydroboration with catecholborane, followed by treatment with easily available reagents such as alkenyl sulfones or alkynyl phenyl sulfones in the presence of a radical initiator, represents an effective and simple one-pot procedure for direct vinylation, formylation, and cyanation.

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Key Words

CC coupling, hydroboration, olefination, radical reactions, vinylsulfones, oximes, alkynes, nitriles, catecholborane

ID: J06-Y2006-2630