A Pyridine-Stabilized N-Phosphinoamidinato N-Heterocyclic Carbene-Diboravinyl Cation: Boron Analogue of Vinyl Cation
Dr. Jun Fan
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, 637371 Singapore
Search for more papers by this authorPei-Ting Chia
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, 637371 Singapore
Search for more papers by this authorZheng-Feng Zhang
Department of Applied Chemistry, National Chiayi University, Chiayi, 60004 Taiwan
Search for more papers by this authorDr. Ming-Chung Yang
Department of Applied Chemistry, National Chiayi University, Chiayi, 60004 Taiwan
Search for more papers by this authorCorresponding Author
Prof. Ming-Der Su
Department of Applied Chemistry, National Chiayi University, Chiayi, 60004 Taiwan
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung, 80708 Taiwan
Search for more papers by this authorCorresponding Author
Dr. Cheuk-Wai So
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, 637371 Singapore
Search for more papers by this authorDr. Jun Fan
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, 637371 Singapore
Search for more papers by this authorPei-Ting Chia
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, 637371 Singapore
Search for more papers by this authorZheng-Feng Zhang
Department of Applied Chemistry, National Chiayi University, Chiayi, 60004 Taiwan
Search for more papers by this authorDr. Ming-Chung Yang
Department of Applied Chemistry, National Chiayi University, Chiayi, 60004 Taiwan
Search for more papers by this authorCorresponding Author
Prof. Ming-Der Su
Department of Applied Chemistry, National Chiayi University, Chiayi, 60004 Taiwan
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung, 80708 Taiwan
Search for more papers by this authorCorresponding Author
Dr. Cheuk-Wai So
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, 637371 Singapore
Search for more papers by this authorAbstract
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+.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
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| ange202212842-sup-0001-compound_7.cif1.2 MB | Supporting Information |
| ange202212842-sup-0001-compound_8.cif1.9 MB | Supporting Information |
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