Borane-Catalyzed Reduction of Pyridines via a Hydroboration/Hydrogenation Cascade

We have developed a method for a B­(C6F5)3-catalyzed hydroboration/hydrogenation cascade reduction of pyridines. The method was particularly effective for 2,3-disubstituted pyridines, which generated piperidines in high yields with high cis selectivity. Mechanistic studies indicated that the pyridin...

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Bibliographic Details
Published inACS catalysis Vol. 11; no. 17; pp. 10824 - 10829
Main Authors Yang, Zhao-Ying, Luo, Heng, Zhang, Ming, Wang, Xiao-Chen
Format Journal Article
LanguageEnglish
Published American Chemical Society 03.09.2021
Subjects
pyridine
piperidine
hydroboration
homogeneous catalysis
hydrogenation
borane
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Summary:We have developed a method for a B­(C6F5)3-catalyzed hydroboration/hydrogenation cascade reduction of pyridines. The method was particularly effective for 2,3-disubstituted pyridines, which generated piperidines in high yields with high cis selectivity. Mechanistic studies indicated that the pyridine substrates and the piperidine products sequentially acted as bases in cooperation with B­(C6F5)3 to split H2. The broad functional group tolerance of the method allowed its use for the synthesis of some biologically active molecules.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.1c02876