Premium
Divergent Coupling of Benzocyclobutenones with Indoles via C−H and C−C Activations
Author(s) -
Lu Hong,
Zhao TianTian,
Bai JinHua,
Ye Dan,
Xu PengFei,
Wei Hao
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202010244
Subject(s) - chemoselectivity , indole test , chemistry , catalysis , selectivity , coupling reaction , combinatorial chemistry , coupling (piping) , divergent synthesis , reaction conditions , stereochemistry , organic chemistry , materials science , metallurgy
Highly selective divergent coupling reactions of benzocyclobutenones and indoles, in which the chemoselectivity is controlled by catalysts, are reported herein. The substrates undergo C2(indole)–C8(benzocyclobutenone) coupling to produce benzylated indoles and benzo[ b ]carbazoles in the Ni‐ and Ru‐catalyzed reactions. A completely different selectivity pattern C2(indole)–C2(benzocyclobutenone) coupling to form arylated indoles is observed in the Rh‐catalyzed reaction. Preliminary mechanistic studies suggest C−H and C−C activations in the reaction pathway. Synthetic utility of this protocol is demonstrated by the selective synthesis of three different types of carbazoles from the representative products.