Synthesis 2007(24): 3839-3845  
DOI: 10.1055/s-2007-1000817
PAPER
© Georg Thieme Verlag Stuttgart · New York

Cobalt-Catalyzed Synthesis of Tertiary Azides from α,α-Disubstituted Olefins under Mild Conditions Using Commercially Available Reagents

Boris Gaspar, Jérôme Waser, Erick M. Carreira*
Laboratorium für Organische Chemie, ETH Hönggerberg, HCI G336, 8093 Zürich, Switzerland
Fax: +41(1)6321328; e-Mail: carreira@org.chem.ethz.ch;
Further Information

Publication History

Received 12 September 2007
Publication Date:
28 November 2007 (online)

Abstract

The use of commercially available azide sources is presented for the cobalt-catalyzed hydroazidation reaction. α,α-Disubstituted olefins with a variety of functional groups were employed as substrates, providing tertiary azides in useful yields.

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Co(BF4)2·6H2O (6 mol%), ligand 2 (6 mol%), alkene (0.5 mmol), azide source (1.5 mmol), t-BuOOH (30 mol%), TMDSO (1 mmol), EtOH (2.5 mL).

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All sulfonyl azides tested in the reaction were provided by Sigma-Aldrich.