Metal-free regio- and chemoselective hydroboration of pyridines catalyzed by 1, 3, 2-diazaphosphenium triflate

Metal-free regio- and chemoselective hydroboration of pyridines catalyzed by 1, 3, 2-diazaphosphenium triflate

N-Heterocyclic phosphenium triflates (NHP-OTf) 1 serve as efficient catalysts for the regio- and chemoselective hydroboration of pyridines under ambient condition with good functional group tolerance. Mechanistic studies indicate that a boronium salt, [(Py)2·Bpin]OTf 4, is generated concomitant with...

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Bibliographic Details
Main Authors: Rao, Bin, Chong, Che Chang, Kinjo, Rei
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry
Catalysts
Catalytic Reactions
Online Access:https://hdl.handle.net/10356/137702
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Institution: Nanyang Technological University
Language: English
Description
Summary:N-Heterocyclic phosphenium triflates (NHP-OTf) 1 serve as efficient catalysts for the regio- and chemoselective hydroboration of pyridines under ambient condition with good functional group tolerance. Mechanistic studies indicate that a boronium salt, [(Py)2·Bpin]OTf 4, is generated concomitant with NHP-H 5 via hydride abstraction from HBpin by 1 in the initial reaction step. Hydride reduction of the activated pyridine in [(Py)2·Bpin]OTf 4 by NHP-H 5 affords the 1,4-hydroboration product selectively. Thus, the phosphenium species act as a hydrogen transfer reagent in the catalytic cycle.

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