Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD<sub>3</sub>SSO<sub>3</sub>Na

Zhao, Lin; Zhou, Xinyu; Zhang, Kemeng; Han, Siyu; Wu, Ge

doi:10.1039/d4qo00858h

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00858h

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Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD₃SSO₃Na

Lin Zhao,

Xinyu Zhou,

Kemeng Zhang

et al.

Abstract: Herein, we describe an electrochemical strategy that enables the aminotrideuteromethylthiolation of isocyanides with anilines and CD3SSO3Na, providing an unprecedented route to access S-CD3 isothioureas in satisfactory yields.

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Cited by 4 publications

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Oxyphosphorodithiolation of Vinyl Azides with P₄S₁₀ and Alcohols Leading to β-Keto Phosphorodithioates

Huang,

Ma,

Sun

et al. 2024

J. Org. Chem.

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A simple strategy for the synthesis of β-keto phosphorodithioates has been developed through the direct oxyphosphorodithiolation of vinyl azides with P 4 S 10 and alcohols in the presence of water. The reaction is conducted at room temperature to provide a number of β-keto phosphorodithioates in moderate to good yields. This methodology has the advantages of simple operation, mild condition, broad substrate scope, and favorable group compatibility.

show abstract

Oxyphosphorodithiolation of Vinyl Azides with P₄S₁₀ and Alcohols Leading to β-Keto Phosphorodithioates

Huang,

Ma,

Sun

et al. 2024

J. Org. Chem.

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Regio- and Stereoselective β-Sulfonylamination of Alkynes via Photosensitized Bifunctional N–S Bond Homolysis

Pu,

Wu,

Cai

et al. 2024

Org. Lett.

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Nitrogen central radicals (NCRs) are versatile synthetic intermediates for creating functional nitrogen-containing molecules. Herein, a photosensitized β-sulfonylamination of terminal alkynes as well as acetylene has been established by employing N-sulfonyl heteroaromatics as bifunctional reagents (BFRs) to efficiently deliver versatile (E)-β-sulfonylvinylamines with excellent regio-and stereoselectivities. Mechanistic studies suggest a base-accelerated energy transfer (EnT) photocatalysis involving aromatic NCR formation, radical addition to alkynes, and sulfonylation processes.β-Sulfonylvinylamines are the most valuable structural backbones of many drugs and bioactive compounds (Figure 1a). 1Traditional synthetic β-sulfonylvinylamines from simple substrates usually undergo multiple steps and require harsh conditions such as high temperature and strong oxidants as well as transition-metal catalysts. 2 Therefore, it remains important to explore efficient protocols to build such skeletons by the convenient transformation of readily available starting materials.

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Electrochemically enabled dearomative [2 + 2] cycloadditions of indoles with alkynes to access cyclobutene-fused indolines

Zi,

Tang,

Wang

et al. 2024

Green Chem.

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Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD₃SSO₃Na

Abstract: Herein, we describe an electrochemical strategy that enables the aminotrideuteromethylthiolation of isocyanides with anilines and CD3SSO3Na, providing an unprecedented route to access S-CD3 isothioureas in satisfactory yields.

Cited by 4 publications

References 30 publications

Oxyphosphorodithiolation of Vinyl Azides with P₄S₁₀ and Alcohols Leading to β-Keto Phosphorodithioates

Oxyphosphorodithiolation of Vinyl Azides with P₄S₁₀ and Alcohols Leading to β-Keto Phosphorodithioates

Regio- and Stereoselective β-Sulfonylamination of Alkynes via Photosensitized Bifunctional N–S Bond Homolysis

Electrochemically enabled dearomative [2 + 2] cycloadditions of indoles with alkynes to access cyclobutene-fused indolines

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Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD3SSO3Na

Abstract: Herein, we describe an electrochemical strategy that enables the aminotrideuteromethylthiolation of isocyanides with anilines and CD3SSO3Na, providing an unprecedented route to access S-CD3 isothioureas in satisfactory yields.

Cited by 4 publications

References 30 publications

Oxyphosphorodithiolation of Vinyl Azides with P4S10 and Alcohols Leading to β-Keto Phosphorodithioates

Oxyphosphorodithiolation of Vinyl Azides with P4S10 and Alcohols Leading to β-Keto Phosphorodithioates

Regio- and Stereoselective β-Sulfonylamination of Alkynes via Photosensitized Bifunctional N–S Bond Homolysis

Electrochemically enabled dearomative [2 + 2] cycloadditions of indoles with alkynes to access cyclobutene-fused indolines

Contact Info

Product

Resources

About

Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD₃SSO₃Na

Oxyphosphorodithiolation of Vinyl Azides with P₄S₁₀ and Alcohols Leading to β-Keto Phosphorodithioates

Oxyphosphorodithiolation of Vinyl Azides with P₄S₁₀ and Alcohols Leading to β-Keto Phosphorodithioates