Activator-Promoted Aryl Halide-Dependent Chemoselective Buchwald–Hartwig and Suzuki–Miyaura Type Cross-Coupling Reactions
Raghu Nath Dhital, Abhijit Sen, Takuma Sato, Hao Hu, Rikako Ishii, Daisuke Hashizume, Hikaru Takaya, Yasuhiro Uozumi, Yoichi M. A. Yamada
Abstract
Herein, we report the development of aryl halide-dependent chemoselective reactions, viz., the Buchwald-Hartwig type coupling reaction of an aryl iodide with an arylboronic acid and an aryl amine in the presence of a heterogeneous and reusable nickel catalyst and the Suzuki-Miyaura type coupling of an aryl chloride under similar conditions. Control experiments revealed that the presence of stoichiometric amounts of the phenylboronic acid/ester and aryl amine are essential for both reactions. NMR and XAFS studies suggested the formation of a boron-amine "ate" complex.
Topics & Concepts
ChemistryHalideArylActivator (genetics)Aryl halideCoupling reactionCombinatorial chemistryCatalysisCoupling (piping)Organic chemistryBiochemistryReceptorAlkylMechanical engineeringEngineeringCatalytic Cross-Coupling ReactionsAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization Methods