Issue 23, 2022

Substitution at sp3 boron of a six-membered NHC·BH3: convenient access to a dihydroxyborenium cation

Abstract

Herein, we have undertaken the synthesis and investigated the reactivity of a 6-membered saturated NHC borane adduct (1). Direct electrophilic halogenation of 1 with a stoichiometric amount of I2 led to NHC boryl iodides, 6-SIDipp·BH2I (2) and 6-SIDipp·BHI2 (3), which were further reacted with various nucleophiles to give novel 6-SIDipp based mono and disubstituted boranes with OTf (4 and 6) or ONO2 (5 and 7) functional groups. The addition of Br2/H2O to 1 smoothly results in a dihydroxyborenium cation (8).

Graphical abstract: Substitution at sp3 boron of a six-membered NHC·BH3: convenient access to a dihydroxyborenium cation

Supplementary files

Article information

Article type
Communication
Submitted
03 Dec. 2021
Accepted
16 Febr. 2022
First published
17 Febr. 2022

Chem. Commun., 2022,58, 3783-3786

Substitution at sp3 boron of a six-membered NHC·BH3: convenient access to a dihydroxyborenium cation

G. Kundu, V. S. Ajithkumar, K. V. Raj, K. Vanka, S. Tothadi and S. S. Sen, Chem. Commun., 2022, 58, 3783 DOI: 10.1039/D1CC06816D

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