Intermolecular Oxidative Amination of Olefins with Amines Catalyzed by the Pd(II)/NPMoV/O₂ System

Abstract

A novel and efficient intermolecular aerobic oxidative amination of electron-deficient olefins with secondary aromatic amines has been successfully achieved by a Pd(II)/NPMoV/HQ-catalyzed reaction under dioxygen.

Silica Gel as a Promoter of Sequential Aza‐Michael/Michael Reactions of Amines and Propiolic Esters: Solvent‐ and Metal‐Free Synthesis of Polyfunctionalized Conjugated Dienes

“…Thus, a further search for efficient methods for the synthesis of this type of compounds is needed. Recently, it has been reported that the metal‐catalyzed oxidative amination of alkenes with secondary amine can give the diene …”

Palladium-Catalyzed Intermolecular Oxidative Amination of Alkenes with Amines, Using Molecular Oxygen as Terminal Oxidant

“…The intermolecular aerobic oxidative amination of electron-deficient olefins with secondary aromatic anilines was successfully achieved using a Pd(II)/NPMoV/HQ-catalyzed reaction with dioxygen [57]. In addition, intermolecular aerobic oxidative allylic amination of simple alkenes with simple amines such as diphenylamine was induced by a Pd(OCOCF 3 ) 2 /NPMoV catalytic system, leading to the corresponding (E)-allylamines in good yields and with good selectivities, through the formation of (η 3 -allyl)palladium(II) trifluoroacetate species as possible key intermediates [58].…”

Palladium Complex Bearing 3,5-Bis(benzotriazol-1-Ylmethyl)toluene Ligand Catalyzes Oxidative Amination of Allyl Butyl Ether

“…This assumption is supported by the presence of one band at 350 cm -1 in the infrared spectrum, assigned to the stretching frequency of the Pd-Cl bond, which is characteristic of a trans dichloride isomer. 40 Considering that a variety of palladium(II) complexes have been successfully studied as catalysts in oxidative amination of alkenes reactions, [25][26][27][28][29][30][31][32][33][34][35][36][37] we tested the behavior of complexes 2 and 3 in the reaction of phthalimide with allyl butyl ether.…”

“…24 On the other hand, a variety of palladium(II) complexes have been successfully studied as catalysts for the aerobic oxidative amination of unactivated alkenes to yield amine derivatives. [25][26][27][28][29][30][31][32][33][34][35][36][37][38] This catalytic reaction leads to the formation of imines or enamines, via b-hydride elimination, through a mechanism analogous to the well-known Wacker process. 25 In this communication we report the synthesis and characterization of the new ligand 3,5-bis(benzotriazol-1-ylmethyl)toluene (1) …”