Allylic Phosphorus Ylides Directly Generated from Alcohols with Water as the only Byproduct

Peizhong Xie; Weishan Fu; Ying Wu; Xinying Cai; Zuolian Sun; Shuangshuang Li; Cuiqing Gao; Xiaobo Yang; Teck Peng Loh

doi:10.1021/acs.orglett.9b01349

Allylic Phosphorus Ylides Directly Generated from Alcohols with Water as the only Byproduct

Peizhong Xie, Weishan Fu, Ying Wu, Xinying Cai, Zuolian Sun, Shuangshuang Li, Cuiqing Gao, Xiaobo Yang, Teck Peng Loh

化学与分子工程学院

科研成果: 期刊稿件 › 文章 › 同行评审

21 引用（Scopus）

摘要

A novel strategy for the preparation of allylic phosphorus ylides directly from Morita-Baylis-Hillman (MBH) alcohols in an environmentally benign manner was developed. With the assistance of a calcium catalyst, the S_N2′ process between phosphines and allylic alcohols occurred smoothly, delivering allylic phosphorus salts and calcium-stabilized hydroxide ions. Then, in situ deprotonation gave the allylic phosphorus ylides with water as the only byproduct. Functionalized 1,3-diene moieties can be conveniently obtained by trapping the ylides through a Wittig olefination.

源语言	英语
页（从-至）	4168-4172
页数	5
期刊	Organic Letters
卷	21
期	11
DOI	https://doi.org/10.1021/acs.orglett.9b01349
出版状态	已出版 - 7 6月 2019

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abstract = "A novel strategy for the preparation of allylic phosphorus ylides directly from Morita-Baylis-Hillman (MBH) alcohols in an environmentally benign manner was developed. With the assistance of a calcium catalyst, the SN2′ process between phosphines and allylic alcohols occurred smoothly, delivering allylic phosphorus salts and calcium-stabilized hydroxide ions. Then, in situ deprotonation gave the allylic phosphorus ylides with water as the only byproduct. Functionalized 1,3-diene moieties can be conveniently obtained by trapping the ylides through a Wittig olefination.",

author = "Peizhong Xie and Weishan Fu and Ying Wu and Xinying Cai and Zuolian Sun and Shuangshuang Li and Cuiqing Gao and Xiaobo Yang and Loh, {Teck Peng}",

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T1 - Allylic Phosphorus Ylides Directly Generated from Alcohols with Water as the only Byproduct

AU - Xie, Peizhong

AU - Fu, Weishan

AU - Wu, Ying

AU - Cai, Xinying

AU - Sun, Zuolian

AU - Li, Shuangshuang

AU - Gao, Cuiqing

AU - Yang, Xiaobo

AU - Loh, Teck Peng

PY - 2019/6/7

Y1 - 2019/6/7

N2 - A novel strategy for the preparation of allylic phosphorus ylides directly from Morita-Baylis-Hillman (MBH) alcohols in an environmentally benign manner was developed. With the assistance of a calcium catalyst, the SN2′ process between phosphines and allylic alcohols occurred smoothly, delivering allylic phosphorus salts and calcium-stabilized hydroxide ions. Then, in situ deprotonation gave the allylic phosphorus ylides with water as the only byproduct. Functionalized 1,3-diene moieties can be conveniently obtained by trapping the ylides through a Wittig olefination.

AB - A novel strategy for the preparation of allylic phosphorus ylides directly from Morita-Baylis-Hillman (MBH) alcohols in an environmentally benign manner was developed. With the assistance of a calcium catalyst, the SN2′ process between phosphines and allylic alcohols occurred smoothly, delivering allylic phosphorus salts and calcium-stabilized hydroxide ions. Then, in situ deprotonation gave the allylic phosphorus ylides with water as the only byproduct. Functionalized 1,3-diene moieties can be conveniently obtained by trapping the ylides through a Wittig olefination.

UR - http://www.scopus.com/inward/record.url?scp=85067007787&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b01349

DO - 10.1021/acs.orglett.9b01349

M3 - 文章

C2 - 31135163

AN - SCOPUS:85067007787

SN - 1523-7060

VL - 21

SP - 4168

EP - 4172

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Allylic Phosphorus Ylides Directly Generated from Alcohols with Water as the only Byproduct

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