Synthesis of Sulfinamidines\nvia Iron-Catalyzed Nitrene\nTransfer Reaction with Sulfenamides

An iron-catalyzed nitrene transfer reaction for the rapid\nsynthesis\nof sulfinamidines from readily available sulfenamides is reported.\nThis method features mild conditions, short reaction times, and a\nbroad substrate scope, allowing the preparation of a variety of sulfinamidines\nin good to excellent yields. The synthetic utility of the sulfinamidine\nproducts was further demonstrated through their conversion to other\nvaluable sulfur(VI) compounds, such as sulfondiimidoyl fluorides,\nsulfinamidiate esters, and sulfonimidamides. Preliminary efforts in\nthe development of an asymmetric variant showed moderate enantioselectivity.

Publication Details

Journal
Figshare
Published
2024-11-18
DOI
https://doi.org/10.1021/acs.joc.4c02286.s001
Primary Topic
Synthesis and Catalytic Reactions
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article
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article

Synthesis of Sulfinamidines\nvia Iron-Catalyzed Nitrene\nTransfer Reaction with Sulfenamides

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Synthesis and Catalytic Reactions
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Synthesis of Sulfinamidines\nvia Iron-Catalyzed Nitrene\nTransfer Reaction with Sulfenamides

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Abstract

An iron-catalyzed nitrene transfer reaction for the rapid\nsynthesis\nof sulfinamidines from readily available sulfenamides is reported.\nThis method features mild conditions, short reaction times, and a\nbroad substrate scope, allowing the preparation of a variety of sulfinamidines\nin good to excellent yields. The synthetic utility of the sulfinamidine\nproducts was further demonstrated through their conversion to other\nvaluable sulfur(VI) compounds, such as sulfondiimidoyl fluorides,\nsulfinamidiate esters, and sulfonimidamides. Preliminary efforts in\nthe development of an asymmetric variant showed moderate enantioselectivity.

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Synthesis and Catalytic Reactions
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Synthesis of Sulfinamidines\nvia Iron-Catalyzed Nitrene\nTransfer Reaction with Sulfenamides · Figshare (2024) | TGRS Research Map | TGRS