Construction of C-P Bonds from Free Cyclobutanone Oximes and Chlorophosphines via Radical-Radical Coupling

Lu Lu Yang; Jiale Wu; Yang Li; Yuhai Tang; Jing Li; Silong Xu

doi:10.1021/acs.orglett.4c00799

Construction of C-P Bonds from Free Cyclobutanone Oximes and Chlorophosphines via Radical-Radical Coupling

Lu Lu Yang
, Jiale Wu
, Yang Li
, Yuhai Tang
, Jing Li
, Silong Xu

School of Chemistry

Xi'an Jiaotong University

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Herein, we report a catalyst-free reaction of cyclobutanone oximes with chlorophosphines (R₂PCl), which forms a fragile C═N-O-PR₂ species that undergoes N-O homolysis, fragmentation, and radical-radical coupling, leading to the formation of cyano-containing phosphine oxides in good yields. The reaction features an in situ activation of cyclobutanone oximes for radical generation, in which R₂PCl plays a dual role as both an activator and a reactant.

Original language	English
Pages (from-to)	3208-3212
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.4c00799
State	Published - 19 Apr 2024

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title = "Construction of C-P Bonds from Free Cyclobutanone Oximes and Chlorophosphines via Radical-Radical Coupling",

abstract = "Herein, we report a catalyst-free reaction of cyclobutanone oximes with chlorophosphines (R2PCl), which forms a fragile C═N-O-PR2 species that undergoes N-O homolysis, fragmentation, and radical-radical coupling, leading to the formation of cyano-containing phosphine oxides in good yields. The reaction features an in situ activation of cyclobutanone oximes for radical generation, in which R2PCl plays a dual role as both an activator and a reactant.",

author = "Yang, \{Lu Lu\} and Jiale Wu and Yang Li and Yuhai Tang and Jing Li and Silong Xu",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

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day = "19",

doi = "10.1021/acs.orglett.4c00799",

language = "英语",

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TY - JOUR

T1 - Construction of C-P Bonds from Free Cyclobutanone Oximes and Chlorophosphines via Radical-Radical Coupling

AU - Yang, Lu Lu

AU - Wu, Jiale

AU - Li, Yang

AU - Tang, Yuhai

AU - Li, Jing

AU - Xu, Silong

PY - 2024/4/19

Y1 - 2024/4/19

N2 - Herein, we report a catalyst-free reaction of cyclobutanone oximes with chlorophosphines (R2PCl), which forms a fragile C═N-O-PR2 species that undergoes N-O homolysis, fragmentation, and radical-radical coupling, leading to the formation of cyano-containing phosphine oxides in good yields. The reaction features an in situ activation of cyclobutanone oximes for radical generation, in which R2PCl plays a dual role as both an activator and a reactant.

AB - Herein, we report a catalyst-free reaction of cyclobutanone oximes with chlorophosphines (R2PCl), which forms a fragile C═N-O-PR2 species that undergoes N-O homolysis, fragmentation, and radical-radical coupling, leading to the formation of cyano-containing phosphine oxides in good yields. The reaction features an in situ activation of cyclobutanone oximes for radical generation, in which R2PCl plays a dual role as both an activator and a reactant.

UR - https://www.scopus.com/pages/publications/85190117799

U2 - 10.1021/acs.orglett.4c00799

DO - 10.1021/acs.orglett.4c00799

M3 - 文章

C2 - 38597783

AN - SCOPUS:85190117799

SN - 1523-7060

VL - 26

SP - 3208

EP - 3212

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Construction of C-P Bonds from Free Cyclobutanone Oximes and Chlorophosphines via Radical-Radical Coupling

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