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Ruthenium(II)‐Catalyzed C−H Activation of Imidamides and Divergent Couplings with Diazo Compounds: Substrate‐Controlled Synthesis of Indoles and 3 H ‐Indoles
Author(s) -
Li Yunyun,
Qi Zisong,
Wang He,
Yang Xifa,
Li Xingwei
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201606316
Subject(s) - diazo , ruthenium , chemistry , catalysis , bond cleavage , acceptor , indole test , cleavage (geology) , intermolecular force , molecule , coupling reaction , substrate (aquarium) , stereochemistry , photochemistry , medicinal chemistry , organic chemistry , physics , oceanography , fracture (geology) , geology , condensed matter physics , geotechnical engineering , engineering
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 3 H ‐indoles under ruthenium catalysis. The coupling of α‐diazoketoesters afforded NH indoles by cleavage of the C(N 2 )−C(acyl) bond whereas α‐diazomalonates gave 3 H ‐indoles by C−N bond cleavage. This reaction constitutes the first intermolecular coupling of diazo substrates with arenes by ruthenium‐catalyzed C−H activation.