The Phospha-Bora-Wittig Reaction

Andryj Borys-Smith; Ella Rice; Gary Nichol; Michael J Cowley

doi:10.1021/jacs.1c06228

The Phospha-Bora-Wittig Reaction

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-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 language	English
Journal	Journal of the American Chemical Society
Early online date	26 Aug 2021
DOIs	https://doi.org/10.1021/jacs.1c06228
Publication status	E-pub ahead of print - 26 Aug 2021

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10.1021/jacs.1c06228

20210830_Cowley_jacs.1c06228Final published version, 0.99 MBLicence: Creative Commons: Attribution-NonCommercial-NoDerivatives (CC BY-NC-ND)

https://pubs.acs.org/doi/10.1021/jacs.1c06228

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title = "The Phospha-Bora-Wittig Reaction",

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.",

author = "Andryj Borys-Smith and Ella Rice and Gary Nichol and Cowley, \{Michael J\}",

year = "2021",

month = aug,

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doi = "10.1021/jacs.1c06228",

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journal = "Journal of the American Chemical Society",

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AU - Borys-Smith, Andryj

AU - Rice, Ella

AU - Nichol, Gary

AU - Cowley, Michael J

PY - 2021/8/26

Y1 - 2021/8/26

N2 - 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.

AB - 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.

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M3 - Article

SN - 0002-7863

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

ER -

The Phospha-Bora-Wittig Reaction

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Bond activation and catalysis with low-valent aluminium

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The Phospha-Bora-Wittig Reaction

Abstract

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Bond activation and catalysis with low-valent aluminium

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