Synlett 2016; 27(08): 1187-1192
DOI: 10.1055/s-0035-1561599
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© Georg Thieme Verlag Stuttgart · New York

Site-Selective and Stereoselective C(sp3)–H Borylation of Alkyl Side Chains of 1,3-Azoles with a Silica-Supported Monophosphine-Iridium Catalyst

Ryo Murakami
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan   Email: sawamura@sci.hokudai.ac.jp
,
Tomohiro Iwai
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan   Email: sawamura@sci.hokudai.ac.jp
,
Masaya Sawamura*
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan   Email: sawamura@sci.hokudai.ac.jp
› Author Affiliations
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Publication History

Received: 28 February 2016

Accepted after revision: 18 March 2016

Publication Date:
30 March 2016 (online)


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Abstract

Site-selective and stereoselective C(sp3)–H borylation of alkyl side chains of 1,3-azoles with bis(pinacolato)diboron was effectively catalyzed by a silica-supported monophosphine-iridium catalyst. The borylation occurred under relatively mild conditions (2 mol% Ir, 50–90 °C), affording the corresponding primary and secondary alkylboronates. This system was applicable to a variety of 1,3-(benzo)azoles such as thiazoles, oxazoles, and imidazoles.

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