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

Bo Jiang; Xing Jun Tu; Xue Wang; Shu Jiang Tu; Guigen Li

doi:10.1021/ol501404x

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

Bo Jiang, Xing Jun Tu, Xue Wang, Shu Jiang Tu, Guigen Li

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

32 Scopus citations

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.

Original language	English
Pages (from-to)	3656-3659
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	14
DOIs	https://doi.org/10.1021/ol501404x
State	Published - Jul 18 2014

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title = "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.",

author = "Bo Jiang and Tu, {Xing Jun} and Xue Wang and Tu, {Shu Jiang} and Guigen Li",

year = "2014",

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T1 - Copper(I)-catalyzed multicomponent reaction providing a new access to fully substituted thiophene derivatives

AU - Jiang, Bo

AU - Tu, Xing Jun

AU - Wang, Xue

AU - Tu, Shu Jiang

AU - Li, Guigen

PY - 2014/7/18

Y1 - 2014/7/18

N2 - 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.

AB - 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.

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U2 - 10.1021/ol501404x

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SP - 3656

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 14

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