4 years ago

Reactivity of the 2-Chloroazaborolyl Anion

Reactivity of the 2-Chloroazaborolyl Anion
Peixing Chen, Chunming Cui
The reactivity of the 2-chloroazaborolyl anion (LBCl)[K(THF)] {1; L = [ArNC(R)CHC(R)]–; Ar = 2,6-Me2C6H3, R = tBu} was investigated. Treatment of 1 with a diazomethane resulted in the formation of a donor-stabilized iminoborane featuring an intramolecular donor-stabilized B=N bond. Compound 1 readily reacted with chlorotriphenyltin to afford the new 1,2-azaborolyl complex 3, whereas reactions with ortho-quinone, azobenzene, and diphenyl disulfide led to the oxidative cycloaddition and cleavage of the disulfide S–S bond, with elimination of KCl.The 2-Chloroazaborolyl anion 1 undergoes salt elimination with diazomethane, Ph3SnCl, ortho-quinone, PhSSPh, and PhN=NPh, and exhibits the borylene-like reactivity originating from the 1,2-azaborole intermediate.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/ejic.201700511

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