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Synlett 2010(11): 1641-1646  
DOI: 10.1055/s-0029-1220128
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Suzuki and Stille Reactions for Regioselective Strategies of Incorporation of the 1,3-Oxazole Heterocycle: Mild Desulfonylation for the Synthesis of C-4 and C-5 Monosubstituted Oxazoles

David R. Williams*, Liangfeng Fu
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, IN 47405-7102, USA
Fax: +1(812)8558300; e-Mail: williamd@indiana.edu;
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Publication History

Received 25 March 2010
Publication Date:
01 June 2010 (online)

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Abstract

Suzuki and Stille cross-coupling reactions are surveyed for site-selective C-4 and C-5 elaboration of 2-(phenylsulfonyl)-1,3-oxazole derivatives. Conditions for mild reductive desulfonylations provide for direct incorporation of the intact oxazole heterocycle through bonding at C-4 and C-5.

Key words

cross-coupling reactions - arylation - alkenylation - reductive desulfonylation

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