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New Twist on a Classic Reaction

Development of the Phospha-Bora-Wittig reaction
Overview of the new reaction

In research funded by the ERC and now reported in the Journal of the American Chemical Society, Dr Michael Cowley and postdoctoral researcher Dr Andryj Borys have developed a new and widely applicable synthetic route to a broad class of compounds called phospha-alkenes.

The reaction is a twist on the classical Wittig reaction, which is widely used in organic synthesis for the preparation of alkenes. This new work promotes phosphorus from helpful assistant in the Wittig reaction – used to remove oxygen to create the alkene C=C double bond – to central character – taking the place of one carbon to create the P=C double bond of phospha-alkenes.

The replacement results in more reactive and highly-coloured compounds which have useful properties but have hitherto been challenging to prepare. This simpler and more general synthetic access to phospha-alkenes will accelerate research into their use in catalysis (reducing the energy cost of chemical synthesis) and as opto-electronically active materials for low-energy displays and solar power generation.

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Monday, October 11, 2021