The Phospha-Bora-Wittig Reaction

[Image: see text] 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–NR(2) reacts with carbonyl compounds to form 1,2,3-phosphaboraoxetanes, analogues of oxaphosphetane intermediates...

Descripción completa

Detalles Bibliográficos
Autores principales: Borys, Andryj M., Rice, Ella F., Nichol, Gary S., Cowley, Michael J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8431359/
https://www.ncbi.nlm.nih.gov/pubmed/34437805
http://dx.doi.org/10.1021/jacs.1c06228
Descripción
Sumario:[Image: see text] 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–NR(2) 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.

Ejemplares similares