Zn-Catalyzed Dehydroxylative Phosphorylation of Allylic Alcohols with P(III)-Nucleophiles

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期刊论文

作者：

Xiong, Biquan*;Shi, Chonghao;Ren, Yining;Xu, Weifeng;Liu, Yu;...

通讯作者：

Xiong, Biquan;Zhu, Longzhi;Cao, F

作者机构：

[Xiong, Biquan; Liu, Yu; Tang, Ke-Wen; Xu, Weifeng; Zhu, Longzhi; Cao, F; Shi, Chonghao; Ren, Yining; Cao, Fan] Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Hunan, Peoples R China.

[Yin, Shuang-Feng] Hunan Univ, Coll Chem & Chem Engn, Adv Catalyt Engn Res Ctr, Minist Educ,State Key Lab Chemo Biosensing & Chemo, Changsha 410082, Hunan, Peoples R China.

[Yin, Shuang-Feng] Cent South Univ Forestry & Technol, Coll Sci, Changsha 410004, Hunan, Peoples R China.

通讯机构：

[Xiong, BQ; Zhu, LZ; Cao, F ] H

Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Hunan, Peoples R China.

语种：

英文

关键词：

Catalysis;Nucleophiles;Phosphorus compounds;Allylic alcohol;Efficient protocols;Functionalized;Optimal reaction condition;Phosphinate;Phosphine oxide;Phosphonates;Scaled-up;Step control;Synthesised;Phosphorylation;1,2 dichloroethane;alcohol derivative;dichloromethane;dimethyl sulfoxide;dioxane;Lewis acid;nucleophile;phosphinate derivative;phosphine oxide derivative;phosphonic acid derivative;solvent;toluene;unclassified drug;zinc;allylation;Arbuzov reaction;Article;catalysis;catalyst;chemical structure;dehydroxylative phosphorylation;phosphorus nuclear magnetic resonance;phosphorylation;reaction analysis;reaction optimization;reaction temperature;synthesis

期刊：

JOURNAL OF ORGANIC CHEMISTRY

ISSN：

0022-3263

年：

2024

卷：

期：

页码：

3033-3048

DOI：

10.1021/acs.joc.3c02489

基金类别：

This work was supported by the National Natural Science Foundation of China (21908050 and 22008061), the Natural Science Foundation of Hunan Province (2023JJ30274 and 2023JJ30275), and the Scientific Research Fund of Hunan Provincial Education Department (23A0497 and 23B0634).

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本校为其他机构

院系归属：

理学院

摘要：

A novel and efficient protocol for the synthesis of diarylallyl-functionalized phosphonates, phosphinates, and phosphine oxides through the zinc-catalyzed dehydroxylative phosphorylation of allylic alcohols with P(III)-nucleophiles via a Michaelis-Arbuzov-type rearrangement is reported. A broad range of allylic alcohols and P(III)-nucleophiles (P(OR)3, ArP(OR)2, and Ar2P(OR)) are well tolerated in this reaction, and the expected dehydroxylative phosphorylation products could be synthesized with good to excellent yields under the optimal reactio...

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Zn-Catalyzed Dehydroxylative Phosphorylation of Allylic Alcohols with P(III)-Nucleophiles

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