Rearrangement of alkynyl sulfoxides catalyzed by gold(I) complexes

被引:284
作者
Shapiro, Nathan D. [1 ]
Toste, F. Dean [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
关键词
D O I
10.1021/ja070789e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of gold(I)-catalyzed rearrangement reactions of alkynyl sulfoxides are reported. Homopropargylsulfoxides are rearranged to benzothiepinones or benzothiopines, while alpha-thioenones are formed in the reaction of propargylsulfoxides. The proposed mechanism proceeds via an alpha-carbonyl gold-carbenoid intermediate formed through gold-promoted oxygen atom transfer from the sulfoxide to the alkyne.
引用
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页码:4160 / +
页数:3
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