2244-48-6Relevant academic research and scientific papers
Iodine-Mediated Cross-Dehydrogenative Coupling of Heterocyclic Thiols with Amines: An Easy and Practical Formation of S?N Bond
Dong, Zhi-Bing,Fan, Yong-Hao,Hao, Er-Jun,Hu, Zhi-Chao,Peng, Kang,Shi, Zhen,Wu, Yue-Xiao
, p. 5889 - 5894 (2021/11/27)
An efficient iodine-mediated construction of S?N bond was developed. Such a cross-dehydrogenative coupling of heterocyclic thiols with amines proceeded smoothly under metal-free and base-free conditions, and afforded a series of sulfenamides in good to excellent yields. The easily available substrates and convenient synthetic procedure illustrate potential synthetic value of this protocol for the preparation of sulfenamide related biologically or pharmaceutically active compounds.
Scalable electrochemical oxidant-and metal-free dehydrogenative coupling of S-H/N-H
Tang, Shanyu,Liu, Yan,Li, Longjia,Ren, Xuanhe,Li, Jiao,Yang, Guanyu,Li, Heng,Yuan, Bingxin
supporting information, p. 1370 - 1374 (2019/02/14)
A practical and scalable electrochemical oxidation of S-H and N-H was developed. This oxidant- and catalyst-free electrochemical process enables S-N bond formation with inexpensive nickel electrodes in an undivided cell. This procedure exhibits broad substrate scopes and good functional-group compatibility. A 50 g scale oxidative coupling augurs well for industrial applications.
Hypervalent iodine(III)-promoted metal-free S-H activation: An approach for the construction of S-S, S-N, and S-C bonds
Rattanangkool, Eakkaphon,Krailat, Watanya,Vilaivan, Tirayut,Phuwapraisirisan, Preecha,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
, p. 4795 - 4804 (2014/08/05)
The activation of the sulfur atom of thiols with (diacetoxyiodo)benzene (DIB) has been explored in the preparation of symmetrical disulfides and sulfenamides. Disulfides can be produced in excellent yields (75-95%) upon treatment of thiols with DIB. The reaction was complete in less than five minutes at room temperature. Aliphatic, aromatic, and heteroaromatic thiols are compatible with this transformation. Moreover, heteroaromatic disulfides obtained from heteroaromatic thiols further reacted with a nucleophilic amine in the presence of a base to provide the corresponding sulfenamides in fair to good yields (43-90%) in a one-pot fashion. The methodology was successfully extended to indole as a representative electron-rich aromatic compound, which allowed successful construction of a S-C bond in one pot. The key benefits of this reaction include lower toxicity, low cost of DIB reagent, and mild reaction conditions (room temperature, undried solvents and open flask).
A New Procedure for the Conversion of Thiols into Reactive Sulfenylating Agents
Barton, D. H. R.,Hesse, R. H.,O'Sullivan, A. C.,Pechet, M. M.
, p. 6697 - 6702 (2007/10/02)
Thiols may be converted in high yield into unsymmetrical 2-pyridyl disulfides 3.Treatment of these with alkylating agents (e.g., alkyl fluorosulfonates or oxonium salts) affords the corresponding N-alkylpyridyl disulfides 4, which are potent sulfenylating agents (Scheme II) and react smoothly with a variety of sulfur nucleophiles (e.g., thiols, thiones, thioamides, dithiocarbamates, thiocyanate, etc.) to afford disulfides, with amines to afford sulfenamides, and with β-diketones to afford sulfides.This new method is particularly well-suited to the preparation of unsymmetrical disulfides and sulfenamides from complex and otherwise r eactive thiols.
