Application of Palladium-Catalyzed Cross-Coupling Reactions in Organic Synthesis

Abstract

: Palladium-catalyzed cross-coupling reactions have gained a continuously growing interest of synthetic organic chemists. The present review gives a brief account of applications of the palladium-catalyzed cross-coupling reactions in comprehensive synthesis, viz., the Heck, Stille, Suzuki–Miyaura, Negishi, Sonogashira, Buchwald–Hartwig, Ullmann and the Oxidative, decarboxylative cross-coupling reactions, with particular emphasis on the synthesis of heterocyclic compounds.

Thiosemicarbazone Complexes of Transition Metals as Catalysts for Cross-Coupling Reactions

“…Since the first report by Sonogashira in 1975 [121], the metal complex-catalysed coupling of terminal alkynes with haloorganics has developed into an essential tool for the synthetic organic chemist (Scheme 24) [1,5,9]. Palladium or copper complexes are generally employed to facilitate this reaction and some very efficient systems have been reported for a wide variety of halides.…”

“…In addition, improvements in catalyst design are continually being made and thus allow the use of milder conditions, immobilisation on solid supports, biphasic systems for ease of separation, more benign solvents, etc. Research in the area of transition metal catalysed carbon-carbon and carbon-heteroatom coupling reactions has led to a wide variety of very efficient and useful procedures which are now most often known by the names of the scientists who pioneered their use such as Suzuki-Miyaura, Mizoroki-Heck, Negishi, Sonogashira, Kumada-Tamao-Corriu, Migita-Kosugi-Stille, Tsuji-Trost, Buchwald-Hartwig [1][2][3][4][5][6][7][8][9]. These procedures are mainly based on palladium although other metals have been shown to be effective in a number of cases.…”

Immobilizing palladium on melamine‐functionalized magnetic nanoparticles: An efficient and reusable phosphine‐free catalyst for Mizoroki–Heck reaction

“…[ 1–3 ] Palladium, one of the most important transition metals in organic synthesis, catalyzes various carbon–carbon coupling reactions, such as Mizoroki–Heck, Suzuki–Miyaura, and Sonogashira–Hagihara reactions. [ 4‐6 ] Among these reactions, the palladium‐catalyzed Mizoroki–Heck reaction of olefins and aryl halides has turned out to be extremely powerful synthetic method for the formation of a wide variety of advanced materials containing CC double bond, such as biologically active heterocycles, agrochemicals, pharmaceuticals, and natural products. [ 7 ]…”

Cp*Co(III)-Catalyzed C–H Hydroarylation of Alkynes and Alkenes and Beyond: A Versatile Synthetic Tool

“…This approach has enabled the synthesis of many compounds of interest, such as natural products, materials, and pharmaceuticals. 1 During the last two decades, palladium(II) has unarguably been in the limelight when accomplishing C–H bond-activation reactions, 2 although other transition metals, such as rhodium(III), 3 ruthenium(II), 4 and iridium(III), 5 have also been capable of efficiently carrying out these kinds of transformations. Nonetheless, the use of the aforementioned second- and third-row-transition metals comes with the disadvantage of toxicity and high cost.…”