Recent advances in heterobimetallic palladium(ii)/copper(ii) catalyzed domino difunctionalization of carbon–carbon multiple bonds

Abstract

The double functionalization of carbon-carbon multiple bonds in one-pot processes has emerged in recent years as a fruitful tool for the rapid synthesis of complex molecular scaffolds. This review covers the advances in domino reactions promoted by the couple palladium(ii)/copper(ii), which was proven to be an excellent catalytic system for the functionalization of substrates.

Intra‐Intermolecular Palladium‐Catalyzed Domino Reactions of Glycine Allylamides for the Synthesis of Diversely Functionalized Piperazinones

“…N-allyl-N-cyclohexylamide 1a was used as the model substrate to screen for the optimal reaction conditions. The initial experiment was carried out under conditions that were previously used by us, [9d] that is, 5 mol-% of PdCl 2 (MeCN) 2 and CuCl 2 (3 equiv. ) in tetrahydrofuran (THF) at reflux (Scheme 1).…”

“…[1] Among these palladium-catalyzed approaches, domino reactions have become a powerful tool to rapidly increase molecular complexity in a single transformation. [2] Great efforts in this field have been made with regard to the development of new syntheses for heterocycles by using procedures based on carboaminations, [3] diaminations, [4] carbooxygenations, [5] dioxygenations, [6] and aminooxygenations. [7] Reactions performed in a doubly intramolecular manner have proven to be useful tools to convert acyclic alkenes and alkynes that contain two nucleophiles into heteropolycyclic products.…”

Advances in Oxosulfonylation Reaction

“…Difunctionalization is a powerful and straightforward strategy to introduce two functional groups in a single reaction to synthesize complex molecular architectures rapidly. [1][2][3][4] Epitomized by the classical Sharpless aminohydroxylation [CÀ O/CÀ N] [5] and dihydroxylation [CÀ O/CÀ O], [6] difunctionalization process is largely utilized for the introduction of two functional groups in adjacent carbons simultaneously to build highly functionalized organic compounds. [7] Over the past few years, representative reactions include carbooxygenation [CÀ C/CÀ O], [8][9][10] oxyhalogenation [CÀ O/Chalide], [11][12][13] and dicarbofunctionalization [CÀ C/ CÀ C] [7,14] reactions have been extensively developed as a powerful method due to its ability to assemble complex skeletons rapidly.…”

Highly Crystallized Pd/Cu Nanoparticles on Activated Carbon: An Efficient Heterogeneous Catalyst for Sonogashira Cross-Coupling Reaction

“…Despite many attempts to develop a transition-metal-catalyzed Sonogashira coupling reaction using a single metal, such as Cu [4,5], Fe [6,7], Ni [8,9], and Au [10][11][12][13][14], most of today's transition-metal-catalyzed cross-coupling chemistry still relies on a bimetallic catalyst system of Pd and Cu. In the putative catalytic cycle of a Sonogashira reaction, Pd and Cu are responsible for the oxidative addition of a C-X bond and the transmetalation of an activated triple bond, respectively [15,16]. The Pd/Cu bimetallic catalyst system has excellent redox properties, probably because of the electron-donating and -accepting characteristics of Cu and Pd, respectively [17,18].…”