1,3-Carboboration of iodonium ylides.

Chem Commun (Camb)

Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, Cymru/Wales CF10 3AT, UK.

Published: March 2020

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.

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http://dx.doi.org/10.1039/c9cc08749dDOI Listing

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