A Completely Metal-Free Protocol for Oxidative Desulfitative C−N Coupling Reaction in Non-Basic Condition

IF 3.3 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Chemistry - An Asian Journal Pub Date : 2025-03-05 DOI:10.1002/asia.202401575

Partha Das, Souvik Mondal, Subhajit Goswami, Aritra Mondal, Dr. Paramita Das, Dr. Suman Ray

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Abstract

A metal free oxidative desulfitative C−N coupling reaction through activation of latent thiol group using hypervalent iodine reagent is being reported in eco-friendly solvent ethanol. Here, the thio-amide group present in 5-alkylidene-rhodanine has been utilized as latent thiol functionality and C−N coupling with amines is realized. The reaction occurs evading the use of metal catalysts, inert atmosphere, high temperature or microwave heating, and strong base which is normally required for metal catalyzed C−N coupling reaction. Pertinently, here poorly nucleophilic aromatic amines react very efficiently. Desulfitative C−N coupling involving free thiol moiety and poorly nucleophilic aromatic amines in metal free condition has never been accomplished in one step, without requiring high temperature microwave heating or strong bases. The reaction occurs at just 50 °C in few hours under ambient atmosphere. Moreover, here no H₂S is released in the environment, since solid sulphur is precipitated out as side product, making this protocol environmentally friendly. Metal free condition, low temperature, use of non-toxic solvent and reagent, prevention of the release of H₂S in the environment make this protocol very much environmentally friendly and highly suitable for C−N coupling in a sustainable way.

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非碱性条件下氧化脱硫C-N偶联反应的完全无金属方案。

报道了用高价碘试剂在环保溶剂乙醇中通过活化潜巯基进行无金属氧化脱硫的C-N偶联反应。在这里，存在于5-烷基-罗丹宁中的硫酰胺基团被用作潜在的硫醇官能团，并实现了C-N与胺的偶联。该反应不需要金属催化剂、惰性气氛、高温或微波加热以及金属催化C-N偶联反应通常需要的强碱。相应地，这里亲核性差的芳香胺反应非常有效。在不需要高温微波加热或强碱的情况下，游离巯基和亲核性差的芳香胺在游离金属条件下的C-N偶联从未一步到位。该反应在环境气氛下仅在50°C下几个小时内发生。此外，由于固体硫作为副产物析出，因此不会向环境中释放H2S，使该方案更加环保。无金属条件，低温，使用无毒溶剂和试剂，防止H2S在环境中的释放，使得该方案非常环保，非常适合可持续的C-N偶联。

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来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).