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^*

^*Corresponding author for this work

Department of Chemistry

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

22 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3878-3885
Number of pages	8
Journal	Tetrahedron
Volume	65
Issue number	19
DOIs	https://doi.org/10.1016/j.tet.2009.02.074
Publication status	Published - 2009 May 9

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2009.02.074

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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",

language = "English",

volume = "65",

pages = "3878--3885",

journal = "Tetrahedron",

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TY - JOUR

T1 - Straightforward and highly efficient catalyst-free regioselective reaction of thiol to β-nitrostyrene

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

Abstract

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