Synthesis of\nSulfenamides via Photoredox N–S\nCoupling of Dialkyl Azodicarboxylates and Thiols

We herein report a photoredox N–S coupling reaction\nbetween\ndialkyl azodicarboxylates and thiols to access sulfenamide scaffolds.\nThis reaction proceeds under mild, green, and operationally simple\nconditions, offering a broad scope of sulfenamides with high yields\nand excellent atom efficiency. Mechanistic investigations revealed\nthis reaction followed a photoinitiated radical pathway in which iodide\nplays a crucial role as both a radical initiator and a single-electron\nreductant.

Publication Details

Journal
Figshare
Published
2024-12-27
DOI
https://doi.org/10.1021/acs.orglett.4c04454.s001
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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Synthesis of\nSulfenamides via Photoredox N–S\nCoupling of Dialkyl Azodicarboxylates and Thiols

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Sulfur-Based Synthesis Techniques
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Synthesis of\nSulfenamides via Photoredox N–S\nCoupling of Dialkyl Azodicarboxylates and Thiols

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Abstract

We herein report a photoredox N–S coupling reaction\nbetween\ndialkyl azodicarboxylates and thiols to access sulfenamide scaffolds.\nThis reaction proceeds under mild, green, and operationally simple\nconditions, offering a broad scope of sulfenamides with high yields\nand excellent atom efficiency. Mechanistic investigations revealed\nthis reaction followed a photoinitiated radical pathway in which iodide\nplays a crucial role as both a radical initiator and a single-electron\nreductant.

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Sulfur-Based Synthesis Techniques
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Synthesis of\nSulfenamides via Photoredox N–S\nCoupling of Dialkyl Azodicarboxylates and Thiols · Figshare (2024) | TGRS Research Map | TGRS