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 σ-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 α-carbonyl alkyl bromides is described, in which the σ-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 α-carbonyl alkyl bromides, including primary, secondary, and tertiary α-bromoalkyl esters, ketones, and amides.
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China).
Jian-Hong
JH
Fan
Wen-Ting
WT
Wei
Ming-Bo
MB
Zhou
Ren-Jie
RJ
Song
Jin-Heng
JH
Li
Heck reactions; alkenes; cross-coupling; indolinones; palladium