Palladium-Catalyzed Oxidative Difunctionalization of Alkenes with α-Carbonyl Alkyl Bromides Initiated through a Heck-type Insertion: A Route to Indolin-2-ones

The oxidative interception of various sigma-alkyl palladium(II) intermediates with additional reagents for the difunctionalization of alkenes is an important research area. A new palladium-catalyzed oxidative difunctionalization reaction of alkenes with alpha-carbonyl alkyl bromides is described, in which the sigma-alkyl palladium(II) intermediate is generated through a Heck insertion and trapped using an aryl C(sp(2))-H bond. This method can be applied to various alpha-carbonyl alkyl bromides, including primary, secondary, and tertiary alpha-bromoalkyl esters, ketones, and amides.