Host: Division of Organic Chemistry, The Pharmaceutical Society of Japan
o-iodoxybenzoic acid (IBX) as a hypervalent iodine compound has a great deal of attention in organic synthesis because IBX is a mild selective, metal-free, and non-toxic oxidation reagent. However, 2-iodosobenzoic acid (IBA), a waste product from oxidations of IBX, often makes it difficult to separate the desired products from the reaction mixture. To solve the problem we have attempted the development of a novel hypervalent iodine organocatalyst with a fluorous tag, fluorous IBX. Oxidation of alcohols in the presence of a catalytic amount of fluorous IBX and Oxone as a co-oxidant resulted in the corresponding carbonyl compounds in good to high yields. The fluorous IBX is readily recovered as insoluble fluorous IBA from the reaction mixture by simple filtration, and can be reused without significant loss of the catalytic activity.
