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31.14.1.18 Method 18: Oxidative Coupling Reactions between Arenethiols and Arenes

DOI: 10.1055/sos-SD-031-00914

Rakitin, O. A.Science of Synthesis, (200731987.

Phenyl and naphthyl ethers readily undergo sulfanylation by benzenethiol in contact with the hypervalent iodine reagent [bis(trifluoroacetoxy)iodo]benzene [phenyliodine(III) bis(trifluoroacetate), PIFA].[‌55‌] The reaction proceeds smoothly in 1,1,1,3,3,3-hexafluoropropan-2-ol, a poorly nucleophilic and polar solvent, under mild conditions without heating or the use of strong Lewis acid catalysts. For example, 4-isopropyl-1-methoxy-2-(phenylsulfanyl)benzene 17 (R1=Me; R2=4-iPr; R3=H) is obtained in this way from 4-isopropylphenyl methyl ether in 63% yield (Scheme 16).[‌55‌]

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