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Synthesis 2010(9): 1521-1525  
DOI: 10.1055/s-0029-1218686
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 1-Substituted 2-(Trifluoromethyl)indoles via a Palladium-Catalyzed Double Amination Reaction

Shu-Xiang Donga, Xing-Guo Zhang*a,b, Qiong Liua, Ri-Yuan Tanga, Ping Zhonga, Jin-Heng Li*a,b
a College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, P. R. of China
b Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research, Hunan Normal University, Changsha 410081, P. R. of China
Fax: +86(577)86689615; e-Mail: zxg@wzu.edu.cn; e-Mail: jhli@hunnu.edu.cn;
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Publication History

Received 21 December 2009
Publication Date:
24 February 2010 (online)

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Abstract

A new, selective protocol for the synthesis of 1-substituted 2-(trifluoromethyl)indoles has been developed by palladium-catalyzed double amination reaction of 2-chloro-1-(2-halophenyl)-3,3,3-trifluoroprop-1-enes with primary amines. This route allows the formation of two C-N bonds in one pot from the reaction between­ 2-chloro-1-(2-halophenyl)-3,3,3-trifluoroprop-1-enes and primary amines using the Pd2(dba)3/L4/t-BuONa system.

Key words

palladium - double amination - 2-chloro-1-(2-halophenyl)-3,3,3-trifluoroprop-1-enes - 2-(trifluoromethyl)indoles

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The structure of the products was determined according to the single-crystal X-ray structure of the product 8.