The Phospha-Bora-Wittig Reaction

04 August 2021, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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-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

Title
Description
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Title
xyzcoordinates
Description
zip file with xyz coordinates of calculated structures.
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Supporting information
Description
how to make the stuff we made and how we know we made it.
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