Oxidation Catalysis by an Aerobically Generated Dess–Martin Periodinane Analogue. (9th May 2018)

• Record Type: Journal Article
• Authors: Maity, Asim; Hyun, Sung‐Min; Wortman, Alan K.; Powers, David C.
• Is Part Of: Angewandte Chemie. Volume 130:Number 24(2018)
• Page Start: 7323
• Page End: 7327
• Publication Date: 2018-05-09
• Subjects: Aerobe Oxidation -- Autoxidation -- Hypervalente Iodverbindungen -- Nachhaltige Chemie; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201804159
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Hypervalent iodine(V) reagents, such as Dess–Martin periodinane (DMP) and 2‐iodoxybenzoic acid (IBX), are broadly useful oxidants in chemical synthesis. Development of strategies to generate these reagents from dioxygen (O2 ) would immediately enable use of O2 as a terminal oxidant in a broad array of substrate oxidation reactions. Recently we disclosed the aerobic synthesis of I(III) reagents by intercepting reactive oxidants generated during aldehyde autoxidation. In this work, aerobic oxidation of iodobenzenes is coupled with disproportionation of the initially generated I(III) compounds to generate I(V) reagents. The aerobically generated I(V) reagents exhibit substrate oxidation chemistry analogous to that of DMP. The developed aerobic generation of I(V) has enabled the first application of I(V) intermediates in aerobic oxidation catalysis.