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 دسمبر 2021
Accepted
16 فرؤری 2022
First published
17 فرؤری 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements