Synlett 2014; 25(11): 1621-1625
DOI: 10.1055/s-0033-1341279
letter
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed sp3 C–H Bond Activation from Decarboxylative Cross­Coupling of α,β-Unsaturated Carboxylic Acids with Amides

Jia-Xiang Zhang
a   Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
,
Yan-Jing Wang
b   College of Sciences, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Fax: +86(10)62554670   eMail: nxwang@mail.ipc.ac.cn
,
Nai-Xing Wang*
a   Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
,
Wei Zhang
a   Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
,
Cui-Bing Bai
a   Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
,
Yi-He Li
a   Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
,
Jia-Long Wen
a   Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
› Institutsangaben
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Publikationsverlauf

Received: 10. März 2014

Accepted after revision: 07. April 2014

Publikationsdatum:
14. Mai 2014 (online)


Abstract

Nickel-catalyzed functionalization of C(sp3)–H bonds adjacent to a nitrogen atom in amides through decarboxylative cross-coupling of α,β-unsaturated carboxylic acids is reported. A possible reaction mechanism is proposed that involves radical intermediate species.

Primary Data

 
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  • 19 Typical Procedure: To a mixture of cinnamic acid (0.148 g, 1 mmol), Ni(OAc)2·4H2O (25 mg, 0.1 mmol), and N,N-dimethylacetamide (2 mL), tert-butyl hydroperoxide (0.39 g, 3 mmol, 70% in water) was added at r.t. dropwise. The resulting mixture was heated to 100 °C for 16 h, then the mixture was added to dichloromethane (40 mL) and washed with water and saturated brine. The organic solution was dried with anhydrous magnesium sulfate and the desired product was separated on a silica gel column (petroleum ether–EtOAc).