Issue 22, 2020
From the journal:

Chemical Communications

1,3-Carboboration of iodonium ylides†‡

Theodore A. Gazis, ORCID logo a   Bayan A. J. Mohajeri Thaker,a   Darren Willcox,ab   Darren M. C. Ould,a   Jan Wenz,a   Jeremy M. Rawson, ORCID logo c   Michael S. Hill, ORCID logo d   Thomas Wirthe  and  Rebecca L. Melen ORCID logo *a  

* Corresponding authors

a Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, Cymru/Wales, UK
E-mail: MelenR@cardiff.ac.uk

b Department of Chemistry, University of Manchester, Oxford Rd, Manchester, UK

c Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Avenue, Windsor, Ontario N9B 3P4, Canada

d Department of Chemistry, University of Bath, Claverton Down, Bath, UK

e School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, Cymru/Wales, UK

Abstract

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

DOI
https://doi.org/10.1039/C9CC08749D
Article type
Communication
Submitted
08 Nov 2019
Accepted
11 Dec 2019
First published
14 Feb 2020
This article is Open Access
Creative Commons BY license

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

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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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