Transition metal-catalyzed decarboxylative cross-coupling reactions

Abstract

Transition metal-catalyzed decarboxylative cross-coupling reactions have recently emerged as a new and important category of organic transformations that find versatile applications in the construction of carbon-carbon and carbon-heteroatom bonds. The use of relatively cheap and stable carboxylic acids to replace organometallic reagents enables the decarboxylative cross-coupling reactions to proceed with good selectivities and functional group tolerance. In the present review we summarize the various types of decarboxylative cross-coupling reactions catalyzed by different transition metal complexes. The scope and applications of these reactions are described. The challenges and opportunities in the field are discussed.

Thermal-reductive transformations of carbon dioxide catalyzed by small molecules using earth-abundant elements

“…Some catalytic systems based on earth-abundant elements such as Ni and Cu have been developed; these were covered extensively as a part of a recent review on the use of CO 2 in organic synthesis [3]. Favorable thermodynamics is a prerequisite for the development of new carboxylative reactions, in which the microscopic reverse process (i.e., decarboxylation) may dominate under some circumstances [47,48].…”

Light driven decarboxylative cross coupling of acrylic acid and iodobenzene using [Mo 132 ] type keplerate as a catalyst

“…However, in order to improve the versatility, cost, and utility of transition-metal-based methods, efforts have led to the development of simple and elegant protocols that employ organic functionality as activation handles for complex coupling reactions. Among different organic coupling reaction decarboxylative cross coupling reaction [13][14][15][16][17] plays an important role because the material used in this method is inexpensive and also stable in normal condition. Thus it is easy to perform such coupling reaction with carboxylic acid.…”

“…Further optimizations of the system and catalyst conditions have made decarboxylative cross-coupling using bimetallic Pd-Cu systems applicable to organic synthesis, most predominantly in the formation of biaryls. The variability of this combined catalytic system allows effective promotion of a large spectrum of reactions, including aryl ketone formation, carbon-heteroatom cross-coupling, and several others [13].…”

Mechanistic studies on the metal-free decarboxylative coupling reaction for synthesis of propargylamines by NMR

“…1,2 As the starting materials, carboxylic acids, are stable and environmentally friendly because they release nontoxic carbon dioxide as the by-product in the coupling reactions. The decarboxylative coupling reaction with aromatic carboxylic acids has been developed since Goossen first reported Pd-catalyzed decarboxylative coupling in 2007.…”