Iodine(V)/RutheniumACHTUNGTRENUNG(III)-Cocatalyzed Oxidations: A Highly Efficient Tandem Catalytic System for the Oxidation of Alcohols and Hydrocarbons with Oxone

摘要

Hypervalent iodine compounds have found wide application as versatile and environmentally friendly oxidizing reagents in synthetic organic chemistry.[1, 2] One of the most impressive recent achievements in the field of organoiodine chemistry is the development of catalytic systems based on hypervalent iodine.[2–4] In particular, the iodine(I)/iodineACHTUNGTRENUNG(III) catalytic cycle based on the oxidation of ArI in situ by using peracids has been utilized for the a functionalization of carbonyl compounds,[3a–d] the oxidative cleavage of alkenes and alkynes,[3e] the TEMPO-mediated oxidation of benzylic alcohols (TEMPO=2,2,6,6-tetramethylpiperidine-1-oxyl),[3f] as well as for various intramolecular cyclizations.[3 gn] Likewise, the iodine(V)-based catalytic cycles that employ Oxone as a stoichiometric oxidant have been used for the oxidation of alcohols,[4a–c] the oxidation of p-alkoxyphenols to quinones,[4d] and the oxidation of benzylic CH bonds (Scheme 1).[4e] However, the synthetic value of the io- ACHTUNGTRENUNGdine(V)-based catalytic cycle is limited by the reoxidation step of iodine(I) or iodineACHTUNGTRENUNG(III) to the iodine(V) species, which proceeds relatively slowly even at temperatures above 70 8C.