Palladium-catalyzed carbonylative coupling reactions between Ar–X and carbon nucleophiles

Abstract

Palladium-catalyzed carbonylative coupling reactions of aromatic halides and related compounds have undergone a rapid development during recent years. Nowadays, a plethora of palladium catalysts are available for the synthesis of ketones, alkynones, chalcones, etc., which are important intermediates in the manufacture of dyes, pharmaceuticals, agrochemicals, and other industrial products. In this critical review, we summarize the development of these carbonylative transformations with carbon nucleophiles (136 references).

An efficient and recyclable thermoregulated phosphine–palladium catalyst for the carbonylative Suzuki coupling of aryl halides with arylboronic acids in water

“…Therefore, many efforts have been devoted to the advancement of this transformation over the past few decades [12][13][14][15][16]. However, the vast majority of the work has been carried out in organic solvents (e.g.…”

The Development and Application of Sulfur Dioxide Surrogates in Synthetic Organic Chemistry

“…[17][18][19] Inspired by this, Willis and co-workers proposed three-component, palladium-catalysed, sulfonylative cross-couplings. Appreciating the known ability of soft sulfur-containing compounds to bind to transition metals, they proposed the paucity of reactions demonstrating metal-catalysed sulfur dioxide incorporation (none of which used aryl-halide-type species, the traditional cross-coupling partners) [5] to be a result of the large excess of gaseous SO 2 poisoning catalytic species.…”

“…Metal-catalysed carbonylations using CO are a particularly powerful method of carbonyl synthesis allowing late-stage convergent construction of complex molecules. [17][18][19] However, the use of pressurised CO vessels presents a significant safety concern; CO surrogates have been particularly successful in advancing this area. One such surrogate is COgen (Scheme 3), an easy-to-handle, stable solid invented by Skrydstrup and coworkers.…”

Carbonylative annulation of unsaturated compounds using molybdenum hexacarbonyl: an efficient synthesis of 2(1H)-quinolones

“…[1][2][3][4][5][6] Introduction of a carbonyl functionality into organic molecules which is pioneered by Heck and co-workers [7][8] and combination of the process with subsequent intramolecular cyclization reactions, have permitted an efficient access to various biologically interesting heterocycles. [9][10][11][12][13][14][15][16] Although carbonylations of a wide spectrum of organometallic reagents have been performed using gaseous carbon monoxide but the use of highly toxic flammable gaseous carbon monoxide is often impractical as it associates with risky and troublesome handling and needs highly specialized equipments.…”