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Synthesis 2013; 45(16): 2241-2244
DOI: 10.1055/s-0033-1338909
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Reaction of Arylboronic Acids with Aliphatic Nitriles: Synthesis of Alkyl Aryl Ketones and 2-Arylbenzofurans

Xingyong Wang
a   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 3250235, P. R. of China   Fax: +86(577)88368280   Email: jiuxichen@wzu.edu.cn   Email: mcl@wzu.edu.cn
,
Xiaodong Wang
a   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 3250235, P. R. of China   Fax: +86(577)88368280   Email: jiuxichen@wzu.edu.cn   Email: mcl@wzu.edu.cn
,
Miaochang Liu*
a   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 3250235, P. R. of China   Fax: +86(577)88368280   Email: jiuxichen@wzu.edu.cn   Email: mcl@wzu.edu.cn
,
Jinchang Ding
a   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 3250235, P. R. of China   Fax: +86(577)88368280   Email: jiuxichen@wzu.edu.cn   Email: mcl@wzu.edu.cn
b   Wenzhou Vocational and Technical College, Wenzhou, 325035, P. R. of China
,
Jiuxi Chen*
a   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 3250235, P. R. of China   Fax: +86(577)88368280   Email: jiuxichen@wzu.edu.cn   Email: mcl@wzu.edu.cn
,
Huayue Wu
a   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 3250235, P. R. of China   Fax: +86(577)88368280   Email: jiuxichen@wzu.edu.cn   Email: mcl@wzu.edu.cn
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Publication History

Received: 31 March 2013

Accepted after revision: 29 April 2013

Publication Date:
11 June 2013 (online)

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Abstract

An efficient palladium-catalyzed addition of arylboronic acids to aliphatic nitriles has been developed, providing a wide range of alkyl aryl ketones in moderate to excellent yields. It is noteworthy that sequential addition and intramolecular annulation reaction of 2-(2-hydroxyphenyl)acetonitriles with arylboronic acids are also conducted smoothly to afford 2-arylbenzofurans in good yields under the standard conditions.

Key words

palladium - aliphatic nitriles - arylboronic acids - alkyl aryl ketones - 2-arylbenzofurans

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