Metal-Free, N-Iodosuccinimide-Induced Regioselective Iodophosphoryloxylation of Alkenes with P(O)−OH Bonds

Biquan Xiong; Shipan Xu; Yu Zhu; Lei Yao; Congshan Zhou; Yu Liu; Ke Wen Tang; Wai Yeung Wong

doi:10.1002/chem.202000575

Metal-Free, N-Iodosuccinimide-Induced Regioselective Iodophosphoryloxylation of Alkenes with P(O)−OH Bonds

Biquan Xiong
, Shipan Xu
, Yu Zhu
, Lei Yao
, Congshan Zhou
, Yu Liu
, Ke Wen Tang
, Wai Yeung Wong

Research output: Journal article publication › Journal article › Academic research › peer-review

7 Citations (Scopus)

Abstract

A simple and efficient method for the regioselective iodophosphoryloxylation of alkenes with P(O)−OH bonds has been established by using NIS (N-iodosuccinimide) as the iodination reagent under transition-metal-free conditions. The present protocol is compatible with different functional groups, and suitable for various alkenes and P(O)−OH compounds. A variety of functionalized β-iodo-1-ethyl phosphinic/phosphoric acid esters are obtained in good to excellent yields, which could be further transformed to diversified building blocks for the synthesis of bioactive compounds, pharmaceuticals and functional materials.

Original language	English
Pages (from-to)	9556-9560
Number of pages	5
Journal	Chemistry - A European Journal
Volume	26
Issue number	43
DOIs	https://doi.org/10.1002/chem.202000575
Publication status	Published - 27 Mar 2020

Keywords

alkenes
iodophosphoryloxylation
phosphorus
synthetic methods
transition-metal-free

ASJC Scopus subject areas

Catalysis
Organic Chemistry

More information

10.1002/chem.202000575

http://hdl.handle.net/10397/100163

Cite this

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title = "Metal-Free, N-Iodosuccinimide-Induced Regioselective Iodophosphoryloxylation of Alkenes with P(O)−OH Bonds",

abstract = "A simple and efficient method for the regioselective iodophosphoryloxylation of alkenes with P(O)−OH bonds has been established by using NIS (N-iodosuccinimide) as the iodination reagent under transition-metal-free conditions. The present protocol is compatible with different functional groups, and suitable for various alkenes and P(O)−OH compounds. A variety of functionalized β-iodo-1-ethyl phosphinic/phosphoric acid esters are obtained in good to excellent yields, which could be further transformed to diversified building blocks for the synthesis of bioactive compounds, pharmaceuticals and functional materials.",

keywords = "alkenes, iodophosphoryloxylation, phosphorus, synthetic methods, transition-metal-free",

author = "Biquan Xiong and Shipan Xu and Yu Zhu and Lei Yao and Congshan Zhou and Yu Liu and Tang, \{Ke Wen\} and Wong, \{Wai Yeung\}",

year = "2020",

month = mar,

day = "27",

doi = "10.1002/chem.202000575",

language = "English",

volume = "26",

pages = "9556--9560",

journal = "Chemistry - A European Journal",

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TY - JOUR

T1 - Metal-Free, N-Iodosuccinimide-Induced Regioselective Iodophosphoryloxylation of Alkenes with P(O)−OH Bonds

AU - Xiong, Biquan

AU - Xu, Shipan

AU - Zhu, Yu

AU - Yao, Lei

AU - Zhou, Congshan

AU - Liu, Yu

AU - Tang, Ke Wen

AU - Wong, Wai Yeung

PY - 2020/3/27

Y1 - 2020/3/27

N2 - A simple and efficient method for the regioselective iodophosphoryloxylation of alkenes with P(O)−OH bonds has been established by using NIS (N-iodosuccinimide) as the iodination reagent under transition-metal-free conditions. The present protocol is compatible with different functional groups, and suitable for various alkenes and P(O)−OH compounds. A variety of functionalized β-iodo-1-ethyl phosphinic/phosphoric acid esters are obtained in good to excellent yields, which could be further transformed to diversified building blocks for the synthesis of bioactive compounds, pharmaceuticals and functional materials.

AB - A simple and efficient method for the regioselective iodophosphoryloxylation of alkenes with P(O)−OH bonds has been established by using NIS (N-iodosuccinimide) as the iodination reagent under transition-metal-free conditions. The present protocol is compatible with different functional groups, and suitable for various alkenes and P(O)−OH compounds. A variety of functionalized β-iodo-1-ethyl phosphinic/phosphoric acid esters are obtained in good to excellent yields, which could be further transformed to diversified building blocks for the synthesis of bioactive compounds, pharmaceuticals and functional materials.

KW - alkenes

KW - iodophosphoryloxylation

KW - phosphorus

KW - synthetic methods

KW - transition-metal-free

UR - https://www.scopus.com/pages/publications/85087611367

U2 - 10.1002/chem.202000575

DO - 10.1002/chem.202000575

M3 - Journal article

AN - SCOPUS:85087611367

SN - 0947-6539

VL - 26

SP - 9556

EP - 9560

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 43

ER -

Metal-Free, N-Iodosuccinimide-Induced Regioselective Iodophosphoryloxylation of Alkenes with P(O)−OH Bonds

Abstract

Keywords

ASJC Scopus subject areas

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