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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Palladium-catalyzed difluoromethylcarbonylation of aryl iodides
Yijie Wei1, Jinxu Dong2, Xiaohong Wen2
1School of Pharmacy, Nanchang University, Nanchang, Jiangxi 330031, China.
Abstract:
We report a palladium-catalyzed carbonylative difluoromethylation of aryl iodides with (DMPU)2Zn(CF2H)2 under CO, providing direct one-pot access to aryl difluoromethyl ketones (DFMKs). Using a Pd(PPh3)4/RuPhos system in DMSO/DMF, a wide range of electron-neutral and electron-rich aryl iodides are efficiently transformed into the corresponding DFMKs. The resulting ketones readily undergo a range of downstream transformations, including Wittig olefination, hydrogenation, cyclization, and reduction. The utility of this methodology is demonstrated through the late-stage modification of pharmacologically important intermediates, such as an AgAChE inhibitor precursor. This scalable and practical protocol offers a versatile route to DFMKs for medicinal chemistry and complex molecule synthesis.
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