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10 α-Oxidation of Carbonyl Compounds

DOI: 10.1055/sos-SD-225-00320

Uyanik, M.; Ishihara, K.Science of Synthesis: Catalytic Oxidation in Organic Synthesis, (20171635.

General Introduction

Carbonyl compounds play a central role in synthetic organic chemistry. The oxidative α-heterofunctionalization of carbonyl compounds enables access to a large number of synthetic building blocks and high-value molecules. In contrast to the traditional coupling process, oxidative coupling reactions proceed via the in situ activation of substrates to form reactive intermediates. To date, a number of oxidation systems using transition-metal catalysis as well as iodine-based redox catalysis have been developed for this purpose. This section describes the catalytic direct α-oxidative coupling of carbonyl compounds with oxygen and nitrogen nucleophiles. Selected examples of direct α-hydroxylation of carbonyl compounds using metal catalysis or organocatalysis with molecular oxygen or peroxides as the oxygen source are also described. α-Heterofunctionalization using electrophilic reagents, such as nitrosoarenes, oxaziridines, azadicarboxylates, iodosylarenes, Selectfluor, N-halosuccinimides, and molecular halogens (X2), is not covered.[‌1‌‌3‌]