Synlett 2017; 28(17): 2325-2329
DOI: 10.1055/s-0036-1588483
letter
© Georg Thieme Verlag Stuttgart · New York

KI/K2S2O8-Mediated α-C–H Sulfenylation of Carbonyl Compounds with (Hetero)Aryl Thiols

Zan Yang, Jiao Li, Jie Hua, Tao Yang*, Jianmin Yi, Congshan Zhou*
  • College of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, P. R. of China   Email: yangtaozcs@126.com   Email: zhoucongsh@126.com
This work was supported by National Natural Science Foundation of China (No. 21476068, 21471053), Innovation Platform Project of Education Bureau of Hunan Province, China (No. 13K101), and Hunan Provincial Innovation Foundation for Postgraduate (No. CX2016B669).
Further Information

Publication History

Received: 04 April 2017

Accepted after revision: 04 June 2017

Publication Date:
13 July 2017 (eFirst)

Abstract

A new and facile KI/K2S2O8-mediated α-C–H sulfenylation of carbonyl compounds with (hetero)aryl thiols was developed for the formation of C–S bond at room temperature. This method provided a simple process for the synthesis of β-keto thioethers in moderate to excellent yields. A variety of carbonyl compounds and (hetero)aryl thiols were tolerated in this reaction.

Supporting Information

 
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  • 12 Procedure for the Synthesis of 2-{Benzo[d]thiazol-2-ylthio}-1-phenylethanone The mixture of acetophenone (1.0 mmol), benzo[d]thiazole-2(3H)-thione (0.5 mmol, 1 equiv), KI (20 mol%), K2S2O8 (0.6 equiv), and DMSO (1 mL) was stirred at r.t. for 24 h. Afterwards, the reaction mixture was washed with aq NaCl (10 ml) and extracted with EtOAc (15 mL, 3×). The obtained top organic layer was dried with anhydrous MgSO4. The mixture was concentrated in vacuo, and the residue was purified by column chromatography on silica gel (EtOAc/n-hexane = 5%) to afford the pure product. White solid (92%). 1H NMR (400 MHz, CDCl3): δ = 8.07–8.05 (m, 2 H), 7.82–7.80 (m, 1 H), 7.54–7.22 (m, 1 H), 7.61 (t, J = 7.6 Hz, 2 H), 7.52–7.39 (m, 2 H), 7.31–7.28 (m, 2 H), 4.97 (s, 2 H). 13C NMR (100 MHz, CDCl3): δ = 192.93, 165.24, 152.81, 135.45, 135.42, 133.81, 128.76, 128.54, 126.02, 124.38, 121.45, 121.04, 40.99.