US EPA

2881403 

Journal Article 

Review 

Recycling and Catalytic Approaches for the Development of a Rare-Metal-Free Synthetic Method Using Hypervalent Iodine Reagent 

Dohi, T 

2010 

Yes 

Chemical and Pharmaceutical Bulletin
ISSN: 0009-2363
EISSN: 1347-5223 

58 

2 

135-142 

English 

20118569 

10.1248/cpb.58.135 

WOS:000274007200001 

Oxidation reactions consist of a number of important transformations in organic synthesis. However, in spite of their utility in both laboratory- and industrial-scale production, oxidations are among the most problematic processes regarding the factors of safety, environmental friendliness, operational simplicity, etc. As oxidants, hypervalent iodines, such as phenyliodine(III) diacetate (PIDA) and phenyliodine(III) bis(trifluoroacetate) (PIFA), are among promising reagents for developing environmentally benign oxidation reactions due to their low toxicities, mild reactivity, ready availability, high stability, and easy handling. Our research objective is, largely in consideration of economic and environmental viewpoints, to enhance the synthetic values of these reagents as useful alternatives to highly toxic heavy-metal oxidants and even rare transition metals by pioneering their efficient utilization methods and unique reactivities. During this study, we have succeeded in the development of new recyclable reagents 1 and their catalytic utilization, and the design of a new chiral reagent 2 and its application to perform asymmetric oxidations. Accordingly, the recycling and catalytic use of a hypervalent iodine reagent became possible in many representative types of oxidative bond-forming reactions, some of which even include key transformations for natural product synthesis. A summary of these important achievements in hypervalent iodine chemistry are described in this review. 

hypervalent iodine; reagent design; recycling; catalyst; asymmetric oxidation; metal-free method