1,3-Carboboration of iodonium ylides

Theodore A. Gazis; Bayan A.J. Mohajeri Thaker; Darren Willcox; Darren M.C. Ould; Jan Wenz; Jeremy M. Rawson; Michael S. Hill; Thomas Wirth; Rebecca L. Melen

doi:10.1039/c9cc08749d

1,3-Carboboration of iodonium ylides

Theodore A. Gazis
, Bayan A.J. Mohajeri Thaker
, Darren Willcox
, Darren M.C. Ould
, Jan Wenz
, Jeremy M. Rawson
, Michael S. Hill
, Thomas Wirth
, Rebecca L. Melen

Department of Chemistry

Cardiff University
University of Manchester
University of Windsor

Research output: Contribution to journal › Article › peer-review

19 Citations (SciVal)

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.

Original language	English
Pages (from-to)	3345-3348
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	22
Early online date	14 Feb 2020
DOIs	https://doi.org/10.1039/c9cc08749d
Publication status	Published - 18 Mar 2020

Funding

We are grateful to the EPSRC (T. A. G. P/L016443/1) and (R. L. M. EP/R026912/1) for funding and the awarding of an EPSRC Early Career Fellowship (R. L. M.). We also thank the Leverhulme Trust (D. W. and R. L. M. RPG-2016-020) and NSERC (J. M. R. DG 2015-05523) for financial support.

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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Cite this

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doi = "10.1039/c9cc08749d",

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AU - Gazis, Theodore A.

AU - Mohajeri Thaker, Bayan A.J.

AU - Willcox, Darren

AU - Ould, Darren M.C.

AU - Wenz, Jan

AU - Rawson, Jeremy M.

AU - Hill, Michael S.

AU - Wirth, Thomas

AU - Melen, Rebecca L.

PY - 2020/3/18

Y1 - 2020/3/18

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85082094267

U2 - 10.1039/c9cc08749d

DO - 10.1039/c9cc08749d

M3 - Article

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AN - SCOPUS:85082094267

SN - 1359-7345

VL - 56

SP - 3345

EP - 3348

JO - Chemical Communications

JF - Chemical Communications

IS - 22

ER -

1,3-Carboboration of iodonium ylides

Abstract

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ASJC Scopus subject areas

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