Straightforward and highly efficient catalyst-free regioselective reaction of thiol to β-nitrostyrene: a concise synthesis of vinyl sulfide and nitro sulfide

Cheng Ming Chu; Zhijay Tu; Pohsi Wu; Chieh Chieh Wang; Ju Tsung Liu; Chun Wei Kuo; Yu Hsuan Shin; Ching Fa Yao

doi:10.1016/j.tet.2009.02.074

Straightforward and highly efficient catalyst-free regioselective reaction of thiol to β-nitrostyrene: a concise synthesis of vinyl sulfide and nitro sulfide

Cheng Ming Chu
, Zhijay Tu
, Pohsi Wu
, Chieh Chieh Wang
, Ju Tsung Liu
, Chun Wei Kuo
, Yu Hsuan Shin
, Ching Fa Yao^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

22 引文斯高帕斯（Scopus）

摘要

Under catalyst-free reaction conditions, solvent-mediated addition of thiol 2 to β-nitrostyrene 1 proceeded with regioselective control to afford either adduct 3 or vinyl sulfide 4 in good to excellent yield. Thermodynamic and autocatalytic reaction mechanisms were proposed to rationalize the products thus formed.

原文	英語
頁（從 - 到）	3878-3885
頁數	8
期刊	Tetrahedron
卷	65
發行號	19
DOIs	https://doi.org/10.1016/j.tet.2009.02.074
出版狀態	已發佈 - 2009 5月 9

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

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10.1016/j.tet.2009.02.074

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@article{52a0e6da9a084c45a0a39e1714469864,

title = "Straightforward and highly efficient catalyst-free regioselective reaction of thiol to β-nitrostyrene: a concise synthesis of vinyl sulfide and nitro sulfide",

abstract = "Under catalyst-free reaction conditions, solvent-mediated addition of thiol 2 to β-nitrostyrene 1 proceeded with regioselective control to afford either adduct 3 or vinyl sulfide 4 in good to excellent yield. Thermodynamic and autocatalytic reaction mechanisms were proposed to rationalize the products thus formed.",

author = "Chu, \{Cheng Ming\} and Zhijay Tu and Pohsi Wu and Wang, \{Chieh Chieh\} and Liu, \{Ju Tsung\} and Kuo, \{Chun Wei\} and Shin, \{Yu Hsuan\} and Yao, \{Ching Fa\}",

note = "Funding Information: This work was a collaborative effort with Dr. Kak-Shan Shia, Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, whose input was invaluable. We gratefully acknowledge the financial support provided by the National Science Council of the Republic of China and National Taiwan Normal University (TOP001). ",

year = "2009",

month = may,

day = "9",

doi = "10.1016/j.tet.2009.02.074",

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volume = "65",

pages = "3878--3885",

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T2 - a concise synthesis of vinyl sulfide and nitro sulfide

AU - Chu, Cheng Ming

AU - Tu, Zhijay

AU - Wu, Pohsi

AU - Wang, Chieh Chieh

AU - Liu, Ju Tsung

AU - Kuo, Chun Wei

AU - Shin, Yu Hsuan

AU - Yao, Ching Fa

N1 - Funding Information: This work was a collaborative effort with Dr. Kak-Shan Shia, Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, whose input was invaluable. We gratefully acknowledge the financial support provided by the National Science Council of the Republic of China and National Taiwan Normal University (TOP001).

PY - 2009/5/9

Y1 - 2009/5/9

N2 - Under catalyst-free reaction conditions, solvent-mediated addition of thiol 2 to β-nitrostyrene 1 proceeded with regioselective control to afford either adduct 3 or vinyl sulfide 4 in good to excellent yield. Thermodynamic and autocatalytic reaction mechanisms were proposed to rationalize the products thus formed.

AB - Under catalyst-free reaction conditions, solvent-mediated addition of thiol 2 to β-nitrostyrene 1 proceeded with regioselective control to afford either adduct 3 or vinyl sulfide 4 in good to excellent yield. Thermodynamic and autocatalytic reaction mechanisms were proposed to rationalize the products thus formed.

UR - https://www.scopus.com/pages/publications/63549105641

UR - https://www.scopus.com/pages/publications/63549105641#tab=citedBy

U2 - 10.1016/j.tet.2009.02.074

DO - 10.1016/j.tet.2009.02.074

M3 - Article

AN - SCOPUS:63549105641

SN - 0040-4020

VL - 65

SP - 3878

EP - 3885

JO - Tetrahedron

JF - Tetrahedron

IS - 19

ER -

Straightforward and highly efficient catalyst-free regioselective reaction of thiol to β-nitrostyrene: a concise synthesis of vinyl sulfide and nitro sulfide

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