Regioselective Reversal in One-Pot and Two-Step Reaction of 1-(2-Hydroxyphenyl)-Propargyl Alcohols with Aryl/Alkyl Mercaptan: Construction of 3-(Alkylthio)benzofurans and 2-(Alkylthiomethyl)benzofurans Starting from Identical Materials

The Cu(MeCN)<sub>4</sub>PF<sub>6</sub>-catalyzed reaction of 1-(2-hydroxyphenyl)-propargyl alcohols with aryl/alkyl mercaptan and subsequent treatment with K<sub>2</sub>CO<sub>3</sub> only offered 3-(alkylthio)benzofurans, whereas the stoichiometric-exceeding CuI-mediated reaction and subsequent treatment with DIPEA furnished 2-(alkylthiomethyl)benzofurans with high selectivity. The amount of Cu(I) salts plays a key role in selective formation. This unique protocol for the selective construction of the two series of benzofurans containing alkylthio group proved to be suitable for broad substrates <b>1</b> and <b>2</b> except for aliphatic alkynyl alcohols.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-12-07
DOI
https://doi.org/10.1021/acs.joc.4c02729
Citations
2
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
0.50

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article

Regioselective Reversal in One-Pot and Two-Step Reaction of 1-(2-Hydroxyphenyl)-Propargyl Alcohols with Aryl/Alkyl Mercaptan: Construction of 3-(Alkylthio)benzofurans and 2-(Alkylthiomethyl)benzofurans Starting from Identical Materials

Yang Zhu, Guisheng Deng
2 citations
The Journal of Organic Chemistry
Catalytic Alkyne Reactions
0.50
article

Regioselective Reversal in One-Pot and Two-Step Reaction of 1-(2-Hydroxyphenyl)-Propargyl Alcohols with Aryl/Alkyl Mercaptan: Construction of 3-(Alkylthio)benzofurans and 2-(Alkylthiomethyl)benzofurans Starting from Identical Materials

Yang Zhu, Guisheng Deng
article en
2 citations

Abstract

The Cu(MeCN)<sub>4</sub>PF<sub>6</sub>-catalyzed reaction of 1-(2-hydroxyphenyl)-propargyl alcohols with aryl/alkyl mercaptan and subsequent treatment with K<sub>2</sub>CO<sub>3</sub> only offered 3-(alkylthio)benzofurans, whereas the stoichiometric-exceeding CuI-mediated reaction and subsequent treatment with DIPEA furnished 2-(alkylthiomethyl)benzofurans with high selectivity. The amount of Cu(I) salts plays a key role in selective formation. This unique protocol for the selective construction of the two series of benzofurans containing alkylthio group proved to be suitable for broad substrates <b>1</b> and <b>2</b> except for aliphatic alkynyl alcohols.

The Journal of Organic ChemistryVol. 89(24)
Hunan Normal University (CN)
Science and Technology Program of Hunan Province
Openalex Percentile: Top 37%
Catalytic Alkyne Reactions
0.50
DOISourceOpenAlex
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Regioselective Reversal in One-Pot and Two-Step Reaction of 1-(2-Hydroxyphenyl)-Propargyl Alcohols with Aryl/Alkyl Mercaptan: Construction of 3-(Alkylthio)benzofurans and 2-(Alkylthiomethyl)benzofurans Starting from Identical Materials — Yang Zhu, Guisheng Deng · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS