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Angew Chem Int Ed Engl. 2016 Sep 19;55(39):11877-81. doi: 10.1002/anie.201606316. Epub 2016 Aug 25.

Ruthenium(II)-Catalyzed C-H Activation of Imidamides and Divergent Couplings with Diazo Compounds: Substrate-Controlled Synthesis of Indoles and 3H-Indoles.

Li Y1,2, Qi Z1, Wang H1, Yang X1,2, Li X3.

Author information

1
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China.
2
University of Chinese Academy of Sciences, Beijing, 100049, China.
3
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China. xwli@dicp.ac.cn.

Abstract

Indoles are an important structural motif that is commonly found in biologically active molecules. In this work, conditions for divergent couplings between imidamides and acceptor-acceptor diazo compounds were developed that afforded NH indoles and 3H-indoles under ruthenium catalysis. The coupling of α-diazoketoesters afforded NH indoles by cleavage of the C(N2 )-C(acyl) bond whereas α-diazomalonates gave 3H-indoles by C-N bond cleavage. This reaction constitutes the first intermolecular coupling of diazo substrates with arenes by ruthenium-catalyzed C-H activation.

KEYWORDS:

C−H activation; diazo compounds; indoles; ruthenium; transition-metal catalysis

PMID:
27558084
DOI:
10.1002/anie.201606316

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