Iodide-Catalyzed Oxidative Coupling Reaction

Recently，iodide-catalyzed oxidative coupling reaction has obtained excitinginterest in organic synthesis. In comparison with tradition metal-catalyzed couplingreactions, it is not require metal-catalyzed. It could reduce the toxicity of metal andprice. It accord with the development of green chemistry’ demanded.This thesis composes with two parts as follows:Firstly, Bu4NI-catalyzed oxidative coupling reaction by C-H bondfunctionalization of aldehyde.We report a new method from aldehydes and tert-butyl hydroperoxide byBu4NI-catalzed metal-free oxidation reaction preparation of tert-butyl peresters.Mechanistic studies suggest that the protocol proceeds via a radical process. Besides,combining the method with the Kharasch-Sosnovsky reaction offers a practicalapproach for the synthesis of allylic esters from simple aldehydes and alkenes via atwo-step one-pot procedure.Secondly, I2-catalyzed oxidative coupling reaction by C-H bond functionalizationof methyl ketones.We report a novel, metal-free and clean oxidative coupling of methyl ketones andamines to α-ketoamides and amides by I2-catalzed oxidation coupling reaction. Incomparison with tradition reactions, it has many advantages in terms of simpleoperation, mild conditions, high yields, substrates easily compassable, and goodfunctional group tolerance, the higher atom economy.