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| The Syntheses of Cycloalkylaryl Sulfides via Copper-catalyzed C—H bond Activation/C—S
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| WU Jiahao, WU Yanghao, SONG Shaorui, YANG Yuheng, XU Yingqian, HUANG Ling*, CHEN Dingben |
| School of Pharmaceutical and Materials Engineering, Taizhou University, Taizhou 318000, China |
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Abstract In order to design a method of using cheap catalyst to achieve C-H bond activation and construct C—S bond. In this paper, copper-catalyzed C—H bond activation/C—S coupling reaction to synthesize a series of cycloalkylaryl sulfide compounds was studied. A series of cycloalkyl aryl sulfide compounds were synthesized via oxidative denitrogenation C—H bond/C—S coupling procedure using arylsulfonyl hydrazide and cycloalkane as raw materials, CuBr as catalyst, di-tert-butyl peroxide(DTBP) as oxidant, reacted at 120 ℃ for 24 hours. The reaction is suitable for cycloalkanes such as cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclododecane and aryl hydrazides with different substituent groups(methoxy, nitro, chlorine, methyl). Eighteen aryl sulfide compounds were synthesized with the yields ranging from 41% to 72%. Their structures were characterized by 1H NMR, 13C NMR and HR-MS.
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Received: 25 May 2022
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