Reciprocal-Activation Strategy for Allylic Sulfination with Unactivated Allylic Alcohols

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

doi:10.1021/acs.orglett.0c01747

Reciprocal-Activation Strategy for Allylic Sulfination with Unactivated Allylic Alcohols

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

School of Chemistry and Moleculai Engineering

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

24 Scopus citations

Abstract

A reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols was developed. In this reaction, the hydrogen bond interaction between allylic alcohols and sulfinic acids allowed for reciprocal activation, which enabled a dehydrative cross-coupling process to occur under mild reaction conditions. This reaction worked in an environmentally friendly manner, yielding water as the only byproduct. A variety of allylic sulfones could be obtained in good to excellent yields with wide functional group tolerance. In gram scale reactions, allylic sulfones could be conveniently isolated in high yield by filtration.

Original language	English
Pages (from-to)	4893-4897
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.0c01747
State	Published - 19 Jun 2020

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title = "Reciprocal-Activation Strategy for Allylic Sulfination with Unactivated Allylic Alcohols",

abstract = "A reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols was developed. In this reaction, the hydrogen bond interaction between allylic alcohols and sulfinic acids allowed for reciprocal activation, which enabled a dehydrative cross-coupling process to occur under mild reaction conditions. This reaction worked in an environmentally friendly manner, yielding water as the only byproduct. A variety of allylic sulfones could be obtained in good to excellent yields with wide functional group tolerance. In gram scale reactions, allylic sulfones could be conveniently isolated in high yield by filtration.",

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

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = jun,

day = "19",

doi = "10.1021/acs.orglett.0c01747",

language = "英语",

volume = "22",

pages = "4893--4897",

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TY - JOUR

T1 - Reciprocal-Activation Strategy for Allylic Sulfination with Unactivated Allylic Alcohols

AU - Xie, Peizhong

AU - Sun, Zuolian

AU - Li, Shuangshuang

AU - Cai, Xinying

AU - Qiu, Ju

AU - Fu, Weishan

AU - Gao, Cuiqing

AU - Wu, Shisheng

AU - Yang, Xiaobo

AU - Loh, Teck Peng

PY - 2020/6/19

Y1 - 2020/6/19

N2 - A reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols was developed. In this reaction, the hydrogen bond interaction between allylic alcohols and sulfinic acids allowed for reciprocal activation, which enabled a dehydrative cross-coupling process to occur under mild reaction conditions. This reaction worked in an environmentally friendly manner, yielding water as the only byproduct. A variety of allylic sulfones could be obtained in good to excellent yields with wide functional group tolerance. In gram scale reactions, allylic sulfones could be conveniently isolated in high yield by filtration.

AB - A reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols was developed. In this reaction, the hydrogen bond interaction between allylic alcohols and sulfinic acids allowed for reciprocal activation, which enabled a dehydrative cross-coupling process to occur under mild reaction conditions. This reaction worked in an environmentally friendly manner, yielding water as the only byproduct. A variety of allylic sulfones could be obtained in good to excellent yields with wide functional group tolerance. In gram scale reactions, allylic sulfones could be conveniently isolated in high yield by filtration.

UR - http://www.scopus.com/inward/record.url?scp=85086584379&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c01747

DO - 10.1021/acs.orglett.0c01747

M3 - 文章

C2 - 32496788

AN - SCOPUS:85086584379

SN - 1523-7060

VL - 22

SP - 4893

EP - 4897

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Reciprocal-Activation Strategy for Allylic Sulfination with Unactivated Allylic Alcohols

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