Transition metal- and catalyst-free one-pot green method for the synthesis of <i>N</i>-sulfonyl amidines <i>via</i> direct reaction of sulfonyl azides with amines

Kaboudin, Babak; Torabi, Saeed; Kazemi, Foad; Aoyama, Hiroshi

doi:10.1039/d0ra04545d

Cited by 7 publications

(1 citation statement)

References 29 publications

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“…On the basis of our experimental results, together studies in literature 41 , a possible reaction mechanism for the formation of sulfonyl amidines is proposed in Scheme 2.…”

Section: Resultssupporting

confidence: 56%

A One-Pot Synthesis of Sulfonyl Amidinesvia Three-Component Reaction Under Mild and Solvent-Free Conditions

Adiche

Abed

2022

JCSR

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A convenient one-pot synthetic protocol for the preparation of sulfonyl amidines has been developed. The procedure combines three-component reaction of sulfonyl azide, methyl propiolate and secondary cyclic amine coupling in one sequence without any solvent or catalyst and at room temperature. The reaction proceeds smoothly and a variety of desired sulfonyl amidines were obtained in moderate to good yields. This protocol has synthetic advantages in terms of low environmental impact and very short reaction time.

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“…On the basis of our experimental results, together studies in literature 41 , a possible reaction mechanism for the formation of sulfonyl amidines is proposed in Scheme 2.…”

Section: Resultssupporting

confidence: 56%

A One-Pot Synthesis of Sulfonyl Amidinesvia Three-Component Reaction Under Mild and Solvent-Free Conditions

Adiche

Abed

2022

JCSR

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Strategies Toward the Catalyst-Free α-C–H Functionalizations of Tertiary Amines

Deb

Baruah

2023

Top Curr Chem (Z)

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Generation and Aerobic Oxidation of Azavinyl Captodative Radicals

Aggarwal,

Richards,

Fokin

2023

J. Am. Chem. Soc.

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We describe a cascade reaction that selectively incorporates oxygen into the carbon−carbon backbone of alkynes using air as the source. The process starts by lithiating readily available, electron-deficient 1,2,3-triazoles, resulting in an amphoteric lithium ketenimine intermediate. This intermediate can react with both electrophiles and nucleophiles. Under the conditions outlined in this study, we generate azavinyl radicals, which are a rare subset of captodative radicals. When exposed to atmospheric oxygen, these radicals efficiently transform into α-oxygenated amidines�a class of compounds that has not been extensively studied. This process uniquely utilizes molecular oxygen without requiring metal or photocatalysts, and it occurs under mild conditions. Our mechanistic studies provide insights into the intricate sequence involved in the formation and selective capture of azavinyl captodative radicals.

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Transition metal- and catalyst-free one-pot green method for the synthesis of N-sulfonyl amidines via direct reaction of sulfonyl azides with amines

Abstract: A green synthesis of N-sulfonyl amidines via the direct reaction of tertiary or secondary amines with sulfonyl azides.

Cited by 7 publications

References 29 publications

A One-Pot Synthesis of Sulfonyl Amidinesvia Three-Component Reaction Under Mild and Solvent-Free Conditions

A One-Pot Synthesis of Sulfonyl Amidinesvia Three-Component Reaction Under Mild and Solvent-Free Conditions

Strategies Toward the Catalyst-Free α-C–H Functionalizations of Tertiary Amines

Generation and Aerobic Oxidation of Azavinyl Captodative Radicals

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