Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation of Pyridines

A metal-free direct hydrogenation of pyridines was successfully realized by using homogeneous borane catalysts generated from alkenes and HB(C6F5)2 via in situ hydroboration. The reaction affords a broad range of piperidines in high yields with excellent cis stereoselectivities.

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Bibliographic Details
Published in:Journal of the American Chemical Society 2013-09, Vol.135 (35), p.12968-12971
Main Authors: Liu, Yongbing, Du, Haifeng
Format: Article
Language:English
Subjects:
Boranes - chemistry
Catalysis
Hydrogenation
Molecular Structure
Piperidines - chemical synthesis
Piperidines - chemistry
Pyridines - chemistry
Stereoisomerism
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Summary:A metal-free direct hydrogenation of pyridines was successfully realized by using homogeneous borane catalysts generated from alkenes and HB(C6F5)2 via in situ hydroboration. The reaction affords a broad range of piperidines in high yields with excellent cis stereoselectivities.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja406761j