Electrochemical multicomponent reaction toward vicinal sulfenyltetrazolation of unactivated alkenes

Zhu, Xiao-Bin; Yu, Yi; Yuan, Yaofeng; Ye, Ke-Yin

doi:10.1039/d3qo01241g

Cited by 5 publications

References 47 publications

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Electrochemically Induced Desulfurization of Thioureas for the Synthesis of Substituted 5‐Aminotetrazoles

Yu,

Hao,

Liu

et al. 2024

Adv Synth Catal

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A one‐pot method has been developed for synthesizing diverse substituted 5‐aminotetrazoles via the electrochemically induced desulfurizative addition‐cyclization of thioureas with azidotrimethylsilane. This methodology enables the construction of C–N and N–N bonds under mild reaction conditions without transition metal catalysts or external oxidizing agents. The applicability of this approach is demonstrated by its broad substrate scope, compatibility with various functional groups, scalability to gram‐scale synthesis, and practicality evidenced by the synthesis of an antibacterial agent

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Electrochemically Induced Desulfurization of Thioureas for the Synthesis of Substituted 5‐Aminotetrazoles

Yu,

Hao,

Liu

et al. 2024

Adv Synth Catal

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Convergent Paired Electrolysis for [3+2] Cycloaddition of Azidotrimethylsilane with N‐Heterocycles

Bankura,

Ghosh,

Biswas

et al. 2024

ChemSusChem

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A widely used method to obtain tetrazoles is through the azide and nitrile [3+2] cycloaddition. However, this process often involves using non‐recyclable transition metals or Lewis acid catalysts and stoichiometric amounts of oxidants and additives, which reduces atom efficiency. We have discovered a convergent paired electrochemical reaction to perform this cycloaddition reaction, without the need for metal catalysts or oxidants. This tetrazolation strategy uses azidotrimethylsilane (TMSN3) and N‐heterocycles in an undivided cell at a constant current. We use a mixture of CH3CN and equivalent amounts of H2O as co‐solvent at room temperature. It is crucial to produce a stoichiometric amount of active hydroxyl ions through the cathodic reduction of water. Cyclic voltammetry (CV) studies and control experiments confirm that the cycloaddition reaction is specific to the electrode electron transfer process, eliminating the need for a mediator to shuttle electrons. This metal‐ and oxidant‐free strategy is highly compatible with different functional groups and produces products with moderate to good yields. We have successfully tetrazolated bioactive compounds at a late stage, scaled up batches efficiently, and synthesized free amino‐containing N‐heterocycles via denitrogenation of tetrazoles.

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Construction of N-Heterocycles via Electrochemically Generated Nitrogen Radicals and Nitrilium Ions

Shi,

2024

Topics in Heterocyclic Chemistry

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Electrochemical multicomponent reaction toward vicinal sulfenyltetrazolation of unactivated alkenes

Abstract: An electrochemical multicomponent reaction (e-MCR) enables the green and sustainable preparation of diverse vicinal sulfenyltetrazolation using the readily available unactivated olefins, thiols, azidotrimethylsilane, and acetonitrile.

Cited by 5 publications

References 47 publications

Electrochemically Induced Desulfurization of Thioureas for the Synthesis of Substituted 5‐Aminotetrazoles

Electrochemically Induced Desulfurization of Thioureas for the Synthesis of Substituted 5‐Aminotetrazoles

Convergent Paired Electrolysis for [3+2] Cycloaddition of Azidotrimethylsilane with N‐Heterocycles

Construction of N-Heterocycles via Electrochemically Generated Nitrogen Radicals and Nitrilium Ions

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