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Synfacts 2010(7): 0751-0751  
DOI: 10.1055/s-0029-1220133
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

α-Arylation-Heteroannulation Route to 2-Amino-1H-indole-3-carboxylates

Contributor(s): Victor Snieckus, Wei Gan
X. Yang, H. Fu*, R. Qiao*, Y. Jiang, Y. Zhao
Tsinghua University, Beijing, Beijing University of Chemical Technology and Tsinghua University, Shenzhen, P. R. of China
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Publication History

Publication Date:
22 June 2010 (online)

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Significance

A synthesis of 2-amino-1H-indole-3-carboxylates by a copper-catalyzed α-arylation-cyclization from the reaction of ortho-halophenyl trifluoroacetyl anilides with 2-cyanoacetates is reported. The product yields range from moderate to excellent. Interestingly, a 4-bromo substituent survives under the reaction conditions, which suggests a coordination step before the oxidative insertion. The reaction also proceeds under ligand-free conditions in a lower yield.