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De Novo Synthesis of Highly Functionalized Benzimidazolones and Benzoxazolones through an Electrochemical Dehydrogenative Cyclization Cascade
Author(s) -
Xu Fan,
Long Hao,
Song Jinshuai,
Xu HaiChao
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201904931
Subject(s) - chemistry , oxidizing agent , regioselectivity , combinatorial chemistry , dehydrogenation , reagent , ring (chemistry) , benzene , catalysis , cascade , bicyclic molecule , molecule , organic chemistry , chromatography
Benzimidazolone and benzoxazolone moieties are important scaffolds in a variety of pharmaceutical molecules. These bicyclic heterocycles are usually prepared from a benzene derivative through the construction of an additional five‐membered heterocyclic ring. We report herein a method that enables the efficient synthesis of highly substituted benzimidazolone and benzoxazolone derivatives by building both the benzene and the heterocyclic rings through a dehydrogenative cyclization cascade. Readily available arylamine‐tethered 1,5‐enynes undergo a biscyclization/dehydrogenation cascade to afford functionalized benzanellated heterocycles in a single step with complete control of regioselectivity. These electricity‐powered oxidative transformations proceed with H 2 evolution, thus obviating the need for transition‐metal‐based catalysts and oxidizing reagents.