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^*

^*Corresponding author for this work

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

24 Citations (Scopus)

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
Publication status	Published - Jun 19 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
Copyright © 2020 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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\}",

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year = "2020",

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

language = "English",

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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.

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JO - Organic Letters

JF - Organic Letters

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ER -

Reciprocal-Activation Strategy for Allylic Sulfination with Unactivated Allylic Alcohols

Abstract

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