Base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides

Biquan Xiong; Qianqian Ye; Xiaofeng Feng; Longzhi Zhu; Tieqiao Chen; Yongbo Zhou; Chak Tong Au; Shuang Feng Yin

doi:10.1016/j.tet.2014.10.013

Base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides

Biquan Xiong, Qianqian Ye, Xiaofeng Feng, Longzhi Zhu, Tieqiao Chen, Yongbo Zhou, Chak Tong Au, Shuang Feng Yin^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

27 Citations (Scopus)

Abstract

A novel base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides has been developed. The protocol is practical, representing a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. A plausible mechanism was proposed for this reaction.

Original language	English
Pages (from-to)	9057-9063
Number of pages	7
Journal	Tetrahedron
Volume	70
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2014.10.013
Publication status	Published - 25 Nov 2014

Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

User-Defined Keywords

Alkyl halides
Base-promoted
O-Deprotonation/alkylation reaction
P(O)-OH compounds

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10.1016/j.tet.2014.10.013

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@article{07a976f4a0e3405f9c72dbc5afebfeaf,

title = "Base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides",

abstract = "A novel base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides has been developed. The protocol is practical, representing a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. A plausible mechanism was proposed for this reaction.",

keywords = "Alkyl halides, Base-promoted, O-Deprotonation/alkylation reaction, P(O)-OH compounds",

author = "Biquan Xiong and Qianqian Ye and Xiaofeng Feng and Longzhi Zhu and Tieqiao Chen and Yongbo Zhou and Au, {Chak Tong} and Yin, {Shuang Feng}",

note = "Funding Information: This work was supported by NSFC ( U1162109 , 21273066 , 21273067 ), Program for Changjiang Scholars and Innovative Research Team in University ( IRT1238 ), and the Fundamental Research Funds for the Central Universities (Hunan University) . CTA thanks HNU (Hunan University) for an adjunct professorship. ",

year = "2014",

month = nov,

day = "25",

doi = "10.1016/j.tet.2014.10.013",

language = "English",

volume = "70",

pages = "9057--9063",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "47",

}

TY - JOUR

T1 - Base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides

AU - Xiong, Biquan

AU - Ye, Qianqian

AU - Feng, Xiaofeng

AU - Zhu, Longzhi

AU - Chen, Tieqiao

AU - Zhou, Yongbo

AU - Au, Chak Tong

AU - Yin, Shuang Feng

N1 - Funding Information: This work was supported by NSFC ( U1162109 , 21273066 , 21273067 ), Program for Changjiang Scholars and Innovative Research Team in University ( IRT1238 ), and the Fundamental Research Funds for the Central Universities (Hunan University) . CTA thanks HNU (Hunan University) for an adjunct professorship.

PY - 2014/11/25

Y1 - 2014/11/25

N2 - A novel base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides has been developed. The protocol is practical, representing a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. A plausible mechanism was proposed for this reaction.

AB - A novel base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides has been developed. The protocol is practical, representing a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. A plausible mechanism was proposed for this reaction.

KW - Alkyl halides

KW - Base-promoted

KW - O-Deprotonation/alkylation reaction

KW - P(O)-OH compounds

UR - http://www.scopus.com/inward/record.url?scp=84922611104&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2014.10.013

DO - 10.1016/j.tet.2014.10.013

M3 - Journal article

AN - SCOPUS:84922611104

SN - 0040-4020

VL - 70

SP - 9057

EP - 9063

JO - Tetrahedron

JF - Tetrahedron

IS - 47

ER -

Base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides

Abstract

Scopus Subject Areas

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