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

Chem Commun (Camb). 2020 Mar 17;56(22):3345-3348. doi: 10.1039/c9cc08749d.

Authors

Theodore A Gazis¹, Bayan A J Mohajeri Thaker¹, Darren Willcox², Darren M C Ould¹, Jan Wenz¹, Jeremy M Rawson³, Michael S Hill⁴, Thomas Wirth⁵, Rebecca L Melen¹

Affiliations

¹ Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, Cymru/Wales CF10 3AT, UK. [email protected].
² Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, Cymru/Wales CF10 3AT, UK. [email protected] and Department of Chemistry, University of Manchester, Oxford Rd, Manchester, M13 9PL, UK.
³ Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Avenue, Windsor, Ontario N9B 3P4, Canada.
⁴ Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK.
⁵ School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, Cymru/Wales CF10 3AT, UK.

PMID: 32090215
DOI: 10.1039/c9cc08749d

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.