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20.8.4.1.1.3 Variation 3: Arylation of Thiocarboxylic Acids

DOI: 10.1055/sos-SD-020-01480

Collier, S. J.Science of Synthesis, (2007201618.

S-Aryl thioesters 54 can be prepared in reasonable yields by treatment of sodium thioacetates or thiobenzoates with dry arenediazonium 1,2-benzenedisulfonimides 53 (Scheme 21).[‌175‌] S-Aryl thioesters can also be prepared from thiocarboxylates and arenediazonium tetrafluoroborates[‌176‌‌178‌] or diaryliodonium salts.[‌179‌] With highly activated aryl halides, such as 1-chloro-2,4-dinitrobenzene, direct displacement of the halide with thiocarboxylate salts gives S-aryl thiocarboxylates in good yields.[‌180‌,‌181‌] With less-activated aryl halides, such as iodopentamethylbenzene, treatment with copper(I) thiocarboxylate salts[‌182‌] in hexamethylphosphoric triamide[‌183‌] gives the expected thiocarboxylic acid S-esters.

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