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Copper(I)-catalyzed multicomponent reaction providing a new access to fully substituted thiophene derivatives.

ABSTRACT: Readily available triethylammonium 1-(2-oxoindolin-3-ylidene)-2-aroylethanethiolates are efficiently converted into a variety of fully substituted thiophene derivatives by copper(I)-catalyzed denitrogenative reactions with terminal alkynes and N-sulfonyl azides. This new reaction simultaneously installs C-N, C-S, and C-C bonds, allowing direct formation of highly functionalized thiophenes with a wide diversity in substituents in a one-pot manner. A plausible mechanism for the domino process is proposed.

SUBMITTER: Jiang B 

PROVIDER: S-EPMC4337423 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature

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Copper(I)-catalyzed multicomponent reaction providing a new access to fully substituted thiophene derivatives.

Jiang Bo B   Tu Xing-Jun XJ   Wang Xue X   Tu Shu-Jiang SJ   Li Guigen G  

Organic letters 20140702 14

Readily available triethylammonium 1-(2-oxoindolin-3-ylidene)-2-aroylethanethiolates are efficiently converted into a variety of fully substituted thiophene derivatives by copper(I)-catalyzed denitrogenative reactions with terminal alkynes and N-sulfonyl azides. This new reaction simultaneously installs C-N, C-S, and C-C bonds, allowing direct formation of highly functionalized thiophenes with a wide diversity in substituents in a one-pot manner. A plausible mechanism for the domino process is p  ...[more]

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