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Synlett 2011(3): 349-356  
DOI: 10.1055/s-0030-1259331
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Aminomethylation via Cyclopalladated-Ferrocenylimine-Complexes-Catalyzed Suzuki-Miyaura Coupling of Aryl Halides with Potassium N,N-Dialkylaminomethyltrifluoroborates

Dapeng Zoua,b, Hongmeng Cuia,b, Lijin Qina,b, Jingya Lib, Yangjie Wu*a, Yusheng Wu*b,c
a Department of Chemistry, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan 450052, P. R. of China
Fax: +86(371)67761837; e-Mail: wyj@mail.zzu.edu;
b Tetranov Biopharm, LLC. 75 Daxue Road, Zhengzhou, Henan 450052, P. R. of China
c Tetranov International, Inc., 100 Jersey Avenue, Suite A340, New Brunswick, NJ 08901, USA
Fax: +1(732)2537327; e-Mail: yusheng.wu@tetranovglobal.com;
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Publication History

Received 31 August 2010
Publication Date:
19 January 2011 (online)

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Abstract

Using cyclopalladated ferrocenylimine complexes (1-3 mol%) as catalysts, the Suzuki-Miyaura coupling of potassium N,N-dialkylaminomethyltrifluoroborates with aryl and heteroaryl halides were carried out in a 10:1 THF-H2O mixture at 80 ˚C in the presence of Cs2CO3 (3.0 equiv) as base, giving the desired cross-coupling products in 14-87% yields. A variety of potassium alkyltrifluoroborates were also examined.

Key words

cyclopalladated ferrocenylimines - aminomethylation - potassium alkyltrifluoroborates - potassium N,N-dialkyaminomethyltrifluoroborates - aryl halides