Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 40, Pages 12224-12227Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201606177
Keywords
boron; heterocycles; homogeneous catalysis; hydrogen; synthetic methods
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Funding
- ERATO program of JST
- Graduate Program for Leaders in Life Innovation (GPLLI)
- JSPS
- Grants-in-Aid for Scientific Research [16J09383] Funding Source: KAKEN
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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.
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