Iron-Catalyzed Oxidative Addition of Alkoxycarbonyl Radicals to Alkenes with Carbazates and Air

摘要

Carbonylation reactions are powerful tools for C-C bond formation in synthetic chemistry. In this area, carbonyl radicals, such as acyl, alkoxycarbonyl, and carbamoyl radicals, are useful reactive intermediates because they enable the direct introduction of a carbonyl moiety, such as ketone, ester, or amide group, into organic compounds by addition to a multiple bond. Many methods for the generation of acyl radicals and reactions of acyl radicals have been reported. Reactions of carbamoyl radicals are relatively well-known, but examples of reactions of alkoxycarbonyl radicals are limited. In general, alkoxycarbonyl and carbamoyl radicals are generated from the corresponding selenides and xan-thates by treatment with a combination of Bu3SnH and an initiator and photoirradiation [Scheme 1, Eq. (1)]. However, these methods have the disadvantage that they require the use of toxic reagents and special equipment.