Issue 33, 2021

Haloboration: scope, mechanism and utility

Abstract

Haloboration, the addition of B–X (X = Cl, Br, I) across an unsaturated moiety e.g., C[double bond, length as m-dash]Y or C[triple bond, length as m-dash]Y (Y = C, N, etc.), is dramatically less utilised than the ubiquitous hydroboration reaction. However, haloboration of alkynes in particular is a useful tool to access ambiphilic 1,2-disubstituted alkenes. The stereochemical outcome of the reaction is easily controlled and the resulting products have proven to be valuable building blocks in organic synthesis and materials chemistry. This review aims at providing the reader with a brief summary of the historic development and of the current mechanistic understanding of this transformation. Recent developments are discussed and select examples demonstrating the use of haloboration products are given with a focus on the major areas, specifically, natural product synthesis and the development of boron-doped polycyclic aromatic hydrocarbons (B-PAHs).

Graphical abstract: Haloboration: scope, mechanism and utility

Article information

Article type
Perspective
Submitted
09 jun 2020
Accepted
07 jul 2020
First published
08 jul 2020
This article is Open Access
Creative Commons BY license

New J. Chem., 2021,45, 14855-14868

Haloboration: scope, mechanism and utility

S. Kirschner, K. Yuan and M. J. Ingleson, New J. Chem., 2021, 45, 14855 DOI: 10.1039/D0NJ02908D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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