The Phospha-Bora-Wittig Reaction

Andryj Borys-Smith, Ella Rice, Gary Nichol, Michael J Cowley*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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.
Original languageEnglish
JournalJournal of the American Chemical Society
Early online date26 Aug 2021
DOIs
Publication statusE-pub ahead of print - 26 Aug 2021

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