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One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines.


ABSTRACT: The Au(III)-catalyzed cyclization of 2-alkynylanilines was combined in a one-pot procedure with the Au(I)-catalyzed C3-selective direct alkynylation of indoles using the benziodoxolone reagent TIPS-EBX to give a mild, easy and straightforward entry to 2-substituted-3-alkynylindoles. The reaction can be applied to unprotected anilines, was tolerant to functional groups and easy to carry out (RT, and requires neither an inert atmosphere nor special solvents).

SUBMITTER: Brand JP 

PROVIDER: S-EPMC3107533 | biostudies-literature | 2011

REPOSITORIES: biostudies-literature

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One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines.

Brand Jonathan P JP   Chevalley Clara C   Waser Jérôme J  

Beilstein journal of organic chemistry 20110504


The Au(III)-catalyzed cyclization of 2-alkynylanilines was combined in a one-pot procedure with the Au(I)-catalyzed C3-selective direct alkynylation of indoles using the benziodoxolone reagent TIPS-EBX to give a mild, easy and straightforward entry to 2-substituted-3-alkynylindoles. The reaction can be applied to unprotected anilines, was tolerant to functional groups and easy to carry out (RT, and requires neither an inert atmosphere nor special solvents). ...[more]

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