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 sk...
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| Published in | Angewandte Chemie International Edition Vol. 61; no. 46; pp. e202212842 - n/a |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
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14.11.2022
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| Edition | International ed. in English |
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| Abstract | 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+.
A pyridine‐stabilized N‐phosphinoamidinato N‐heterocyclic carbene‐diboravinyl cation was obtained through the displacement reaction of the bromide substituent on a diborene derivative using pyridine. This newly formed species was shown to be a boron analogue of the vinyl cation which could be used for the activation of small molecules. |
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| AbstractList | 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+.
A pyridine‐stabilized N‐phosphinoamidinato N‐heterocyclic carbene‐diboravinyl cation was obtained through the displacement reaction of the bromide substituent on a diborene derivative using pyridine. This newly formed species was shown to be a boron analogue of the vinyl cation which could be used for the activation of small molecules. 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+. 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+ .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+ . 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 B pyridine center is the predominant nucleophilic center and the predominant electrophilic center is either the activated pyridine para position or the B NHC center, illustrating the presence of diborene cation A , borylene‐borenium cation B and diborene‐pyridinium cation C resonance structures in cation 2 + . |
| Author | Zhang, Zheng‐Feng Yang, Ming‐Chung Chia, Pei‐Ting Fan, Jun So, Cheuk‐Wai Su, Ming‐Der |
| Author_xml | – sequence: 1 givenname: Jun surname: Fan fullname: Fan, Jun organization: Nanyang Technological University – sequence: 2 givenname: Pei‐Ting surname: Chia fullname: Chia, Pei‐Ting organization: Nanyang Technological University – sequence: 3 givenname: Zheng‐Feng surname: Zhang fullname: Zhang, Zheng‐Feng organization: National Chiayi University – sequence: 4 givenname: Ming‐Chung surname: Yang fullname: Yang, Ming‐Chung organization: National Chiayi University – sequence: 5 givenname: Ming‐Der surname: Su fullname: Su, Ming‐Der email: midesu@mail.ncyu.edu.tw organization: Kaohsiung Medical University – sequence: 6 givenname: Cheuk‐Wai orcidid: 0000-0003-4816-9801 surname: So fullname: So, Cheuk‐Wai email: CWSo@ntu.edu.sg organization: Nanyang Technological University |
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| Snippet | A boron analogue of vinyl cation, pyridine‐stabilized N‐phosphinoamidinato N‐heterocyclic carbene (NHC)‐diboravinyl cation 2+, was synthesized by displacement... A boron analogue of vinyl cation, pyridine‐stabilized N ‐phosphinoamidinato N ‐heterocyclic carbene (NHC)‐diboravinyl cation 2 + , was synthesized by... A boron analogue of vinyl cation, pyridine-stabilized N-phosphinoamidinato N-heterocyclic carbene (NHC)-diboravinyl cation 2+ , was synthesized by displacement... |
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| SubjectTerms | Boron Carbenes Cations Computer applications Diborene Pyridines Pyridinium Small Molecule Activation Vinyl Cation |
| Title | A Pyridine‐Stabilized N‐Phosphinoamidinato N‐Heterocyclic Carbene‐Diboravinyl Cation: Boron Analogue of Vinyl Cation |
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