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Tris(pentafluorophenyl)borane‐Catalyzed Acceptorless Dehydrogenation of N‐Heterocycles
Author(s) -
Kojima Masahiro,
Kanai Motomu
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201606177
Subject(s) - dehydrogenation , chemistry , catalysis , borane , yield (engineering) , combinatorial chemistry , tris , metal , organic chemistry , reactivity (psychology) , materials science , medicine , biochemistry , alternative medicine , pathology , metallurgy
Catalytic acceptorless dehydrogenation is an environmentally benign way to desaturate organic compounds. This process is traditionally accomplished with transition‐metal‐based catalysts. Herein, a borane‐catalyzed, metal‐free acceptorless dehydrogenation of saturated N‐heterocycles is disclosed. Tris(pentafluorophenyl)borane was identified as a versatile catalyst, which afforded several synthetically important N‐heteroarenes in up to quantitative yield. Specifically, the present metal‐free catalytic system exhibited a uniquely high tolerance toward sulfur functionalities, and demonstrated superior reactivity in the synthesis of benzothiazoles compared to conventional metal‐catalyzed systems. This protocol can thus be regarded as the first example of metal‐free acceptorless dehydrogenation in synthetic organic chemistry.