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From BN-Naphthalenes to Benzoborole Dianions.

Authors
  • Zhu, Dezhao1
  • Guo, Lulu1
  • Li, Jianfeng1
  • Cui, Chunming1
  • 1 State Key Laboratory of Elemento-Organic Chemistry and College of Chemistry, Nankai University, Tianjin, 300071, China. , (China)
Type
Published Article
Journal
Chemistry - A European Journal
Publisher
Wiley (John Wiley & Sons)
Publication Date
Jul 02, 2021
Volume
27
Issue
37
Pages
9514–9518
Identifiers
DOI: 10.1002/chem.202101178
PMID: 33909296
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

The synthesis of benzoborole dianions by alkali metal reduction of BN-naphthalene derivatives via a ring-contraction strategy has been developed. Reduction of 1-alkynyl 2,1-benzazaborine 1 a in Et2 O led to the elimination of alkynyllithium with the formation of 1-amino-1-benzoborole trilithium salt 2 a, whereas reduction of 1-phenyl 2,1-benzazaborine 1 c in THF yielded 1-phenyl-1-benzoborole dilithium salt 2 c with the elimination of ArNHLi. The trilithium and dilithium salts 2 a and 2 c have been fully characterized. Treatment of trilithium salt 2 a with Et3 NHCl led to the selective protonation of the amino lithium to afford the dilithium salt 2 aH, which could be cleanly oxidized to 1-amino-1-benzoborole 3 in an excellent yield. Reaction of 1-phenyl-1-benzoborole dilithium salt 2 c with MeI yielded the lithium borate 4 c, which is luminescent both in solution and in the solid state. © 2021 Wiley-VCH GmbH.

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