Catalyst‐Controlled Dual Reactivity of Sulfonimidamides: Synthesis of Propargylamines and <i>N</i>‐Propargyl Sulfonimidamides

Jesin, C. P. Irfana; Nandi, Ganesh Chandra

doi:10.1002/chem.201805000

Chemistry A European J

2018

DOI: 10.1002/chem.201805000

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Catalyst‐Controlled Dual Reactivity of Sulfonimidamides: Synthesis of Propargylamines and N‐Propargyl Sulfonimidamides

C. P. Irfana Jesin

Ganesh Chandra Nandi

Abstract: Sulfonimidamides (SIAs) are acting both as surrogate amines and nucleophiles depending on the reaction conditions to access propargylamines and N‐propargyl SIAs, respectively. The amine part of SIAs has been cleaved in an InCl3‐catalyzed three‐component A3 coupling reaction with aldehyde and acetylene to yield propargylamine. Moreover, N‐propargyl SIAs were obtained via the direct‐imination of propargyl alcohols in the presence of BF3⋅OEt2.

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Cited by 12 publications

References 27 publications

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Direct Synthesis of Sulfonimidoyl Guanidines from Sulfonimidoyl Azides under Dual (Cobalt and Photoredox) Catalysis

et al. 2022

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A visible‐light (456 nm) promoted dual catalytic (cobalt‐/photoredox) method for the direct synthesis of sulfonimidoyl guanidine via three‐component reaction of aryl amine, isonitrile and sulfonimidoyl azide (as nitrene source) is developed. The protocol is fast, mild and provides products with a wide range of substrates in 56–86% yields. Additionally, the replacement of aryl amine with alcohol and thiol as nucleophile leads to the formation of sulfonimidoyl isourea and sulfonimidoyl isothiourea respectively, which are not yet reported in the literature.

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Direct Synthesis of Sulfonimidoyl Guanidines from Sulfonimidoyl Azides under Dual (Cobalt and Photoredox) Catalysis

et al. 2022

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Visible Light Mediated Co‐Catalyzed Isocyanide Insertion with Sulfonyl Azide: Synthesis of Sulfonyl Carbamimidic Azide and Sulfonyl Aminotetrazole via Carbodiimide Intermediate

Ravindra,

Natarajan,

Padma Priya

et al. 2023

Chemistry A European J

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Herein, we report an operationally simple and efficient protocol to prepare sulfonyl carbamimidic azide and N‐sulfonyl aminotetrazole via Co‐catalyzed three component coupling of sulfonyl azide (acts as nitrene source), isocyanide, and TMS‐azide at room temperature under visible light. Initially, the carbamimidic azide is formed, which cyclizes only in the presence of base to deliver N‐sulfonyl aminotetrazole in very good yields. The sulfonyl aminotetrazole can also be synthesized directly without isolating the carbamimidic azide in the presence of base. The sulfonyl azide is anticipated to generate nitrene and reacts with isocyanide to produce carbodiimide. Subsequent addition of azide (TMS‐N3) to carbodiimide results in the formation of carbamimidic azide.

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Oligomerization: An Inherent Property of Sulfonimidamides?

2020

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The treatment of the TBS-protected p-toluenesulfonimidamide with HCl exclusively affords the deprotected product. However, when HCl was replaced with formic acid, and the reaction mixture was left for an extended time or treated at high temperature, a mixture of oligomers was obtained as main products. The relevant N,N′-capped oligomers were prepared through carbamoylation with p-chlorophenyl isocyanate. The key to dicarbamoylation is to remove formic acid from the reaction mixture. For comparison, methylsulfonimidamide (as the representative of alkyl sulfonimidamides) was tested under sim-[a] Dr.

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Catalyst‐Controlled Dual Reactivity of Sulfonimidamides: Synthesis of Propargylamines and N‐Propargyl Sulfonimidamides

Cited by 12 publications

References 27 publications

Direct Synthesis of Sulfonimidoyl Guanidines from Sulfonimidoyl Azides under Dual (Cobalt and Photoredox) Catalysis

Direct Synthesis of Sulfonimidoyl Guanidines from Sulfonimidoyl Azides under Dual (Cobalt and Photoredox) Catalysis

Visible Light Mediated Co‐Catalyzed Isocyanide Insertion with Sulfonyl Azide: Synthesis of Sulfonyl Carbamimidic Azide and Sulfonyl Aminotetrazole via Carbodiimide Intermediate

Oligomerization: An Inherent Property of Sulfonimidamides?

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