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

Access to Document

10.1021/ol501404x

Cite this

@article{5635c73ae5ca4184a6ad1e4e43ef08b7,

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",

month = jul,

day = "18",

doi = "10.1021/ol501404x",

language = "English",

volume = "16",

pages = "3656--3659",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "14",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=84904541735&partnerID=8YFLogxK

U2 - 10.1021/ol501404x

DO - 10.1021/ol501404x

M3 - Article

C2 - 24988049

AN - SCOPUS:84904541735

VL - 16

SP - 3656

EP - 3659

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 14

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this