Synthesis 2013; 45(1): 118-126
DOI: 10.1055/s-0032-1317849
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Tandem Carbocyclization–Suzuki Coupling Reactions of Trifluoromethyl-Containing Building Blocks Leading to 2-Trifluoromethyl­indenes

Wen-Ying Wang
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, P. R. of China   Fax: +86(577)86689615   Email: zxg@wzu.edu.cn
,
Lei-Lei Sun
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, P. R. of China   Fax: +86(577)86689615   Email: zxg@wzu.edu.cn
,
Chen-Liang Deng
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, P. R. of China   Fax: +86(577)86689615   Email: zxg@wzu.edu.cn
,
Ri-Yuan Tang
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, P. R. of China   Fax: +86(577)86689615   Email: zxg@wzu.edu.cn
,
Xing-Guo Zhang*
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, P. R. of China   Fax: +86(577)86689615   Email: zxg@wzu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 20 September 2012

Accepted after revision: 19 November 2012

Publication Date:
11 December 2012 (online)


Abstract

A palladium-catalyzed tandem carbocyclization–Suzuki coupling is described leading to the synthesis of trifluoromethyl-containing indenes in moderate to good yields. The reactions take place in the presence of palladium(II) acetate, a phosphorus-containing­ ligand [dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine] and potassium carbonate in toluene as the solvent. The process occurs via intramolecular carbocyclization and subsequent Suzuki coupling of the ortho-(2-chlorovinyl)-alkynylbenzenes with arylboronic acids.

 
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