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2.2.1.2.1.2 2-Iodylbenzenesulfonic Acid Catalyzed Oxidation of Alcohols

DOI: 10.1055/sos-SD-225-00023

Singh, F. V.; Wirth, T.Science of Synthesis: Catalytic Oxidation in Organic Synthesis, (2017149.

The scope of 2-iodylbenzenesulfonic acid (51; IBS) has not been well-explored due to stability issues, although its synthesis was reported in 2006.[‌94‌] In 2009, Ishihara and co-workers generated 2-iodylbenzenesulfonic acid (51) in situ from sodium 2-iodobenzenesulfonate (75) and used it as catalyst in the oxidation of alcohols.[‌84‌] Interestingly, 2-iodylbenzenesulfonic acid (51) shows better catalytic activity than 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (50) for these oxidations. The same research group investigated the 2-iodylbenzenesulfonic acid (51) catalyzed oxidative dehydrogenation of cycloalkanols 74 to give α,β-unsaturated ketones 76 using sodium 2-iodobenzenesulfonate (75) as precatalyst and Oxone as terminal oxidant (Scheme 23).[‌84‌] All the oxidation reactions are smooth and the products 76 are isolated in good to excellent yields.

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