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- Title
Hypervalent Iodine(III)-Promoted Metal-Free S-H Activation: An Approach for the Construction of S-S, S-N, and S-C Bonds.
- Authors
Rattanangkool, Eakkaphon; Krailat, Watanya; Vilaivan, Tirayut; Phuwapraisirisan, Preecha; Sukwattanasinitt, Mongkol; Wacharasindhu, Sumrit
- Abstract
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).
- Subjects
HYPERVALENCE (Theoretical chemistry); IODINE compounds; SULFUR; THIOLS; BENZENE; DISULFIDES; SULFENAMIDES
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 22, p4795
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201402180