We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Tris(pentafluorophenyl)borane-Catalyzed Acceptorless Dehydrogenation of N-Heterocycles.
- Authors
Kojima, Masahiro; Kanai, Motomu
- Abstract
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.
- Subjects
NITROGEN compounds; DEHYDROGENATION; METAL catalysts; REACTIVITY (Chemistry); BENZENE compound synthesis
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 40, p12412
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201606177