Palladium-Catalyzed Arylthiolation of Alkynes Enabled by Surmounting Competitive Dimerization of Alkynes

By overcoming the unwanted catalytic dimerization of terminal alkynes, palladium-catalyzed carbothiolation of alkynes with heteroaryl sulfides has been accomplished to provide the corresponding β-heteroaryl alkenyl sulfides with high regio- and stereoselectivity. The key for the preferential arylthi...

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Bibliographic Details
Published in:Organic letters 2019-10, Vol.21 (20), p.8295-8299
Main Authors: Uno, Daisuke, Nogi, Keisuke, Yorimitsu, Hideki
Format: Article
Language:English
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Summary:By overcoming the unwanted catalytic dimerization of terminal alkynes, palladium-catalyzed carbothiolation of alkynes with heteroaryl sulfides has been accomplished to provide the corresponding β-heteroaryl alkenyl sulfides with high regio- and stereoselectivity. The key for the preferential arylthiolation is the use of arylsulfanyl segments, instead of alkylsulfanyl, for smooth C­(heteroaryl)–SR1 bond cleavage and/or of alkylacetylenes that are reluctant to undergo the dimerization. The reaction proceeds under mild and neutral conditions, with various functionalities being thus tolerated.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03056