Issue 22, 2020

1,3-Carboboration of iodonium ylides


Herein, we disclose the utilisation of iodonium ylides to access a range of boron dienolates. Heating of acyclic iodonium ylides in the presence of different aryl boranes leads to the formation of rare 1,3-carboboration products. This methodology could not be expanded to cyclic iodonium ylides which instead formed a Lewis acid–base adduct. Products proved to be remarkably stable under a wide range of conditions allowing for their long term storage.

Graphical abstract: 1,3-Carboboration of iodonium ylides

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Article information

Article type
08 Nov 2019
11 Dec 2019
First published
14 Feb 2020
This article is Open Access
Creative Commons BY license

Chem. Commun., 2020,56, 3345-3348

1,3-Carboboration of iodonium ylides

T. A. Gazis, B. A. J. Mohajeri Thaker, D. Willcox, D. M. C. Ould, J. Wenz, J. M. Rawson, M. S. Hill, T. Wirth and R. L. Melen, Chem. Commun., 2020, 56, 3345 DOI: 10.1039/C9CC08749D

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