Catalyst Selection Facilitates the Use of Heterocyclic Sulfinates as General Nucleophilic Coupling Partners in Palladium-Catalyzed Coupling Reactions

A range of 5- and 6-membered heterocycle-derived sulfinates are shown to be effective nucleophilic coupling partners with aryl chlorides and bromides using Pd(0) catalysis. The use of optimal reaction conditions, specifically incorporating a P­(t-Bu)2Me-derived Pd catalyst, allowed reactions to be p...

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Bibliographic Details
Published in:Organic letters 2017-11, Vol.19 (22), p.6033-6035
Main Authors: Markovic, Tim, Rocke, Benjamin N., Blakemore, David C., Mascitti, Vincent, Willis, Michael C.
Format: Article
Language:English
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Summary:A range of 5- and 6-membered heterocycle-derived sulfinates are shown to be effective nucleophilic coupling partners with aryl chlorides and bromides using Pd(0) catalysis. The use of optimal reaction conditions, specifically incorporating a P­(t-Bu)2Me-derived Pd catalyst, allowed reactions to be performed at moderate temperatures and enabled the inclusion of a variety of sensitive functional groups. Challenging heterocyclic sulfinates, including pyrazine, pyridazine, pyrimidine, pyrazole, and imidazole, were all shown to perform well.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02944