The Phospha-Bora-Wittig Reaction

10 June 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Here, we report the phospha-bora-Wittig reaction for the direct preparation of phosphaalkenes from aldehydes, ketones, esters, or amides. The transient phosphaborene Mes*P=B-NR2 reacts with carbonyl compounds to form 1,2,3-phosphaboraoxetanes, analogues of oxaphosphetane intermediates in the classical Wittig reaction. 1,2,3-phosphaboraoxetanes undergo thermal or Lewis acid/base-promoted cycloreversion, yielding phosphaalkenes. Experimental and density functional theory studies reveal far-reaching similarities between classical and phospha-bora-Wittig reactions.

Keywords

phosphorus
boron
phosphaalkenes
wittig
phospha Wittig
bora Wittig
Phospha-Bora-Wittig
main-group
multiple bonds
mechanism

Supplementary materials

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Supporting Information - final
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