Aerobic Oxidations and Related Reactions Catalyzed by N-Hydroxyphthalimide

Aerobic Oxidations and Related Reactions Catalyzed by N-Hydroxyphthalimide 

Yasutaka Ishii, Satoshi Sakaguchi, and Yasushi Obora 

Recently, we have developed an innovative strategy for the catalytic generation of a type of carbon radical from hydrocarbons. This is a phthalimide N-oxyl (PIN O) radical generated in situ from N-hydroxyphthalimide (NHPI) and molecular oxygen in the presence (or absence) of a cobalt ion under mild conditions. The carbon radicals, derived from a variety of hydrocarbons under the influence of molecular oxygen, lead to oxygenated products like alcohols, ketones, and carboxylic acids in good yields. The development of NHPI-catalyzed reactions has been reported in review papers [7]. 

Here we show a novel methodology for the functionalizations of hydrocarbons, including oxygenation, nitration, sulfoxidation, epoxidation, carboxylation, and oxyalkylation through generation of the catalytic carbon radical. In particular, the NHPI-catalyzed aerobic oxidations of alkanes, which are very important in industry worldwide, are described in detail. 

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