Copper-catalyzed cross-dehydrogenative coupling of N-arylacrylamides with chloroform using tert-butyl peroxybenzoate as oxidant for the synthesis of trichloromethylated 2-oxindoles

Chun Wo Chan; Pui Yiu Lee; Wing Yiu Yu

doi:10.1016/j.tetlet.2015.03.109

Copper-catalyzed cross-dehydrogenative coupling of N-arylacrylamides with chloroform using tert-butyl peroxybenzoate as oxidant for the synthesis of trichloromethylated 2-oxindoles

Chun Wo Chan, Pui Yiu Lee, Wing Yiu Yu

Research output: Journal article publication › Journal article › Academic research › peer-review

24 Citations (Scopus)

Abstract

A Cu-catalyzed cross-dehydrogenative coupling of N-arylacrylamides with chloroform is achieved using tert-butyl peroxybenzoate as oxidant, and trichloromethylated oxindoles were obtained in excellent yield and regioselectivity. This reaction should proceed by cascade CCl3radical CC addition and aryl cyclization.

Original language	English
Pages (from-to)	2559-2563
Number of pages	5
Journal	Tetrahedron Letters
Volume	56
Issue number	20
DOIs	https://doi.org/10.1016/j.tetlet.2015.03.109
Publication status	Published - 13 May 2015

Keywords

2-Oxindole
CH activation
Cross-dehydrogenative coupling
Cyclization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2015.03.109

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title = "Copper-catalyzed cross-dehydrogenative coupling of N-arylacrylamides with chloroform using tert-butyl peroxybenzoate as oxidant for the synthesis of trichloromethylated 2-oxindoles",

abstract = "A Cu-catalyzed cross-dehydrogenative coupling of N-arylacrylamides with chloroform is achieved using tert-butyl peroxybenzoate as oxidant, and trichloromethylated oxindoles were obtained in excellent yield and regioselectivity. This reaction should proceed by cascade CCl3radical CC addition and aryl cyclization.",

keywords = "2-Oxindole, CH activation, Cross-dehydrogenative coupling, Cyclization",

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Copper-catalyzed cross-dehydrogenative coupling of N-arylacrylamides with chloroform using tert-butyl peroxybenzoate as oxidant for the synthesis of trichloromethylated 2-oxindoles. / Chan, Chun Wo; Lee, Pui Yiu; Yu, Wing Yiu.
In: Tetrahedron Letters, Vol. 56, No. 20, 13.05.2015, p. 2559-2563.

Research output: Journal article publication › Journal article › Academic research › peer-review

TY - JOUR

T1 - Copper-catalyzed cross-dehydrogenative coupling of N-arylacrylamides with chloroform using tert-butyl peroxybenzoate as oxidant for the synthesis of trichloromethylated 2-oxindoles

AU - Chan, Chun Wo

AU - Lee, Pui Yiu

AU - Yu, Wing Yiu

PY - 2015/5/13

Y1 - 2015/5/13

N2 - A Cu-catalyzed cross-dehydrogenative coupling of N-arylacrylamides with chloroform is achieved using tert-butyl peroxybenzoate as oxidant, and trichloromethylated oxindoles were obtained in excellent yield and regioselectivity. This reaction should proceed by cascade CCl3radical CC addition and aryl cyclization.

AB - A Cu-catalyzed cross-dehydrogenative coupling of N-arylacrylamides with chloroform is achieved using tert-butyl peroxybenzoate as oxidant, and trichloromethylated oxindoles were obtained in excellent yield and regioselectivity. This reaction should proceed by cascade CCl3radical CC addition and aryl cyclization.

KW - 2-Oxindole

KW - CH activation

KW - Cross-dehydrogenative coupling

KW - Cyclization

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U2 - 10.1016/j.tetlet.2015.03.109

DO - 10.1016/j.tetlet.2015.03.109

M3 - Journal article

SN - 0040-4039

VL - 56

SP - 2559

EP - 2563

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 20

ER -

Copper-catalyzed cross-dehydrogenative coupling of N-arylacrylamides with chloroform using tert-butyl peroxybenzoate as oxidant for the synthesis of trichloromethylated 2-oxindoles

Abstract

Keywords

ASJC Scopus subject areas

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