Sulfination of Unactivated Allylic Alcohols via Sulfinate-Sulfone Rearrangement

3 Citations (Scopus)

Abstract

A dehydrative cross-coupling of unactivated allylic alcohols with sulfinic acids was achieved under catalyst-free conditions. This reaction proceeded via allyl sulfination and concomitant allyl sulfinate-sulfone rearrangement. Various allylic sulfones could be obtained in good to excellent yields with water as the only byproduct. This study expands the synthetic toolbox for constructing allylic sulfone molecules.

Original language	English
Pages (from-to)	8895-8900
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	49
DOIs	https://doi.org/10.1021/acs.orglett.3c03709
Publication status	Published - Dec 15 2023
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2023 American Chemical Society

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.3c03709

Cite this

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title = "Sulfination of Unactivated Allylic Alcohols via Sulfinate-Sulfone Rearrangement",

abstract = "A dehydrative cross-coupling of unactivated allylic alcohols with sulfinic acids was achieved under catalyst-free conditions. This reaction proceeded via allyl sulfination and concomitant allyl sulfinate-sulfone rearrangement. Various allylic sulfones could be obtained in good to excellent yields with water as the only byproduct. This study expands the synthetic toolbox for constructing allylic sulfone molecules.",

author = "Yan Wang and Guangming Wu and Kaiyu Yan and Jiaheng Qin and Rui Liu and Nannan Rong and Yongming Tang and Loh, {Teck Peng} and Peizhong Xie",

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doi = "10.1021/acs.orglett.3c03709",

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TY - JOUR

T1 - Sulfination of Unactivated Allylic Alcohols via Sulfinate-Sulfone Rearrangement

AU - Wang, Yan

AU - Wu, Guangming

AU - Yan, Kaiyu

AU - Qin, Jiaheng

AU - Liu, Rui

AU - Rong, Nannan

AU - Tang, Yongming

AU - Loh, Teck Peng

AU - Xie, Peizhong

PY - 2023/12/15

Y1 - 2023/12/15

N2 - A dehydrative cross-coupling of unactivated allylic alcohols with sulfinic acids was achieved under catalyst-free conditions. This reaction proceeded via allyl sulfination and concomitant allyl sulfinate-sulfone rearrangement. Various allylic sulfones could be obtained in good to excellent yields with water as the only byproduct. This study expands the synthetic toolbox for constructing allylic sulfone molecules.

AB - A dehydrative cross-coupling of unactivated allylic alcohols with sulfinic acids was achieved under catalyst-free conditions. This reaction proceeded via allyl sulfination and concomitant allyl sulfinate-sulfone rearrangement. Various allylic sulfones could be obtained in good to excellent yields with water as the only byproduct. This study expands the synthetic toolbox for constructing allylic sulfone molecules.

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U2 - 10.1021/acs.orglett.3c03709

DO - 10.1021/acs.orglett.3c03709

M3 - Article

C2 - 38059565

AN - SCOPUS:85180005287

SN - 1523-7060

VL - 25

SP - 8895

EP - 8900

JO - Organic Letters

JF - Organic Letters

IS - 49