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

被引：16

作者：

Uno, Daisuke ^{[1
]}

Nogi, Keisuke ^{[1
]}

Yorimitsu, Hideki ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 20期

关键词：

TERMINAL ALKYNES; C-S; BOND FORMATION; REGIOSELECTIVE CYANOTHIOLATION; STEREOSELECTIVE DIMERIZATION; CARBOTHIOLATION; CARBON; ALKYNYLTHIOLATION; FUNCTIONALIZATION; CARBOPALLADATION;

D O I：

10.1021/acs.orglett.9b03056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By overcoming the unwanted catalytic dimerization of terminal alkynes, palladium-catalyzed carbothiolation of alkynes with heteroaryl sulfides has been accomplished to provide the corresponding beta-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.

引用

页码：8295 / 8299

页数：5

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