TfOH-catalyzed three-component synthesis of Dithiocarbamates from α-Diazoesters under continuous flow conditions

Wang, Rui; He, Hangli; Yan, Qiongjiao; Wang, Wei; Wang, Haifeng; Chen, Fen‐Er

doi:10.1007/s41981-022-00249-7

J Flow Chem

2022

DOI: 10.1007/s41981-022-00249-7

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TfOH-catalyzed three-component synthesis of Dithiocarbamates from α-Diazoesters under continuous flow conditions

Rui Wang

Hangli He

Qiongjiao Yan

et al.

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Cited by 7 publications

References 43 publications

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Emerging Trends for the Direct Synthesis of Dithiocarbamates

He,

Zhou,

Liu

2024

Adv Synth Catal

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Dithiocarbamates are common structural motifs in various bioactive compounds, attracting considerable attention due to their wide‐ranging applications in organic synthesis, material science, agrochemicals, and the pharmaceutical industry. Given the significant bioactivity and extensive applications of dithiocarbamates, the continuous pursuit of their efficient and diverse synthetic methods remains critical and urgent. Direct dithiocarbamation reactions can introduce ‐S‐C(S)NR2 group directly into parent molecules, providing shorter, greener, and more practical pathways for the synthesis of organodithiocarbamates. This article offers a comprehensive overview of the latest advancements in direct dithiocarbamation reactions, categorizing them based on the different sources of the ‐S‐C(S)NR2 group, with a particular emphasis on elucidating substrate scope and reaction mechanisms. Additionally, some synthetic limitations and applications of these methods are discussed. This review aims to provide the latest advancements in this field to both general readers and professional practitioners, inspiring innovative ideas for the synthesis of organosulfur compounds.

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Emerging Trends for the Direct Synthesis of Dithiocarbamates

He,

Zhou,

Liu

2024

Adv Synth Catal

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TfOH‐Catalyzed Regioselective Alkylation of Hydroxybenzotriazole with Diazo Compounds and Further Base‐Facilitated Elimination under Batch and Flow Conditions

Luo,

Wang,

et al. 2024

Asian J Org Chem

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An efficient and fascinating strategy has been devised for the construction of N‐hydroxybenzotriazole (HOBt) derivatives and α‐ketoesters via TfOH‐catalyzed regioselective alkylation of N‐hydroxybenzotriazole (HOBt) and one‐pot dehydrogenation oxidation of alkylation products process under batch and flow conditions. It thus provides an expedient approach to access a range of HOBt derivatives and α‐ketoesters in good yields with high regioselectivity under mild conditions. Using flow process, less reacting time, being more environmental friendly, and process continuity ensuring higher operation safety are achieved, highlighting the practicality of the developed system.

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Rapid and General Access to α‐Halogenated Carbonyl Compounds Using Amidine Halide Salts as Halogen Sources under Mild Conditions

Li,

Luo,

Liu

et al. 2024

Eur J Org Chem

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Rapid and efficient construction of α‐haloketones with diazo compounds and amidine·HX (X = Cl, Br, I) salts as halogen sources has been recognized as a simple and practical strategy. The reaction exhibits a broad scope and scalability, thereby enabling synthesis of a broad spectrum of functionally orchestrated α‐haloketones under mild and metal‐free conditions in a short time. Control experiments established the involvement of triffate 11 in the mechanism

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TfOH-catalyzed three-component synthesis of Dithiocarbamates from α-Diazoesters under continuous flow conditions

Cited by 7 publications

References 43 publications

Emerging Trends for the Direct Synthesis of Dithiocarbamates

Emerging Trends for the Direct Synthesis of Dithiocarbamates

TfOH‐Catalyzed Regioselective Alkylation of Hydroxybenzotriazole with Diazo Compounds and Further Base‐Facilitated Elimination under Batch and Flow Conditions

Rapid and General Access to α‐Halogenated Carbonyl Compounds Using Amidine Halide Salts as Halogen Sources under Mild Conditions

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