A pyridine-stabilized N-phosphinoamidinato N-heterocyclic carbene-diboravinyl cation: boron analogue of vinyl cation

A pyridine-stabilized N-phosphinoamidinato N-heterocyclic carbene-diboravinyl cation: boron analogue of vinyl cation

A boron analogue of vinyl cation, pyridine-stabilized N-phosphinoamidinato N-heterocyclic carbene (NHC)-diboravinyl cation 2+ , was synthesized by displacement of bromide in diborene 1 with excess pyridine. Experimental and computational studies showed that the positive charge is mainly at the B-B s...

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Bibliographic Details
Main Authors: Fan, Jun, Chia, Pei-Ting, Zhang, Zheng-Feng, Yang, Ming-Chung, Su, Ming-Der, So, Cheuk-Wai
Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
Format: Article
Language:English
Published: 2023
Subjects:
Science::Chemistry
Boron
Diborene
Online Access:https://hdl.handle.net/10356/164639
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Institution: Nanyang Technological University
Language: English
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Summary:A boron analogue of vinyl cation, pyridine-stabilized N-phosphinoamidinato N-heterocyclic carbene (NHC)-diboravinyl cation 2+ , was synthesized by displacement of bromide in diborene 1 with excess pyridine. Experimental and computational studies showed that the positive charge is mainly at the B-B skeleton with delocalization to the pyridine ligand. One of the main modes of reactivity is through the B=B double bond alongside activation of the pyridine substituent, where the Bpyridine center is the predominant nucleophilic center and the predominant electrophilic center is either the activated pyridine para position or the BNHC center, illustrating the presence of diborene cation A, borylene-borenium cation B and diborene-pyridinium cation C resonance structures in cation 2+ .

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