Non-directed Pd-catalysed C–H arylation of [2.2]paracyclophane

Abstract

We report herein the palladium-catalysed mono-selective C–H arylation of [2.2]paracyclophane (PCP) with diverse aryl iodides in the absence of any pendant directing groups, providing a straightforward and modular access to...

Palladium Catalysis: Dependence of the Efficiency of C−C Bond Formation on Carboxylate Ligand and Alkali Metal Carboxylate or Carboxylic Acid Additive. Part A: the C(sp2)−C(sp2), C(sp2)−C(sp3) and C(sp3)−C(sp3) Bonds

“…The Heck reaction of [2.2]paracyclophane with phenyl iodide has been studied using different Pd catalysts and silver carboxylates (Scheme 2l). [26] The best result arose with PdCl 2 (PCy 3 ) 2 and AgOAc in hexafluoroisopropanol, dichloromethane and trifluoroacetic acid leading to lower yields. With this catalyst, no reaction occurred in the absence of the silver salt.…”

Synthesis of [2.2]Paracyclophane-Fused Heterocycles via Palladium-Catalyzed C–H Activation/Annulation of [2.2]Paracyclophanecarboxamides with Arynes

“…In the past two decades, transition-metal-catalyzed C–H functionalization has witnessed a booming development, and been successfully employed to access [2.2]­paracyclophane derivatives . Meanwhile, palladium-catalyzed intramolecular C–H activation offers an efficient pathway to afford [2.2]­paracyclophane-fused heterocycles by introducing appropriate coupling partners tethered to the [2.2]­paracyclophane backbone (Scheme b). , Nevertheless, the lower catalytic efficiency due to the constraint by the sterically hindered configuration of the [2.2]­paracyclophane skeleton and the limited types of the tethering coupling partners restrict their further applications.…”