Palladium and Copper Catalyzed Sonogashira cross Coupling an Excellent Methodology for C-C Bond Formation over 17 Years: A Review

Abstract

Sonogashira coupling involves coupling of vinyl/aryl halides with terminal acetylenes catalyzed by transition metals, especially palladium and copper. This is a well known reaction in organic synthesis and plays a role in sp2-sp C-C bond formations. This cross coupling was used in synthesis of natural products, biologically active molecules, heterocycles, dendrimers, conjugated polymers and organic complexes. This review paper focuses on developments in the palladium and copper catalyzed Sonogashira cross coupling achieved in recent years concerning substrates, different catalyst systems and reaction conditions.

Microwave-Assisted Synthesis of Quinazolines and Quinazolinones: An Overview

“…Although the aforementioned reactions are considered as the most important transition-metal catalyses, a plethora of vital reactions can be effectively catalyzed by various transition metals including reductive elimination, oxidative addition, and transmetallation. Transition metal catalysis has also found extensive applications in the convenient and efficient synthesis of a wide variety of heterocyclic systems (Ma et al, 2017 ; Ramanathan and Liu, 2017 ; Tiwari and Bhanage, 2017 ; Chatterjee et al, 2018 ; Saikia et al, 2018 ; Chen et al, 2020 ; Debabrata et al, 2020 ; Ghosh et al, 2020 ; Janardhanan et al, 2020 ; Jiang et al, 2020 ; Kanwal et al, 2020 ; Kojima and Matsunaga, 2020 ; Li and Zhang, 2020 ; Nagata and Obora, 2020 ; Neto and Zeni, 2020a , b ; Pal et al, 2020 ; Ratmanova et al, 2020 ; Sahiba and Agarwal, 2020 ; Sonawane et al, 2020 ; Xuan et al, 2020 ). However, the literature survey revealed only an example of zinc (Shi et al, 2004 ), a limited number of iron-catalyzed (Melvin et al, 1992 ; Valderrama et al, 1999 ; Kanth et al, 2006 ; Yin et al, 2012 ; Gopalaiah et al, 2017 , 2019 ; Raut and Bhanage, 2017 ; Eidi et al, 2018 ), and relatively more copper-catalyzed reactions, leading to the synthesis of quinazoline and quinazolinone derivatives (Melvin et al, 1992 ; Chatterjee et al, 2018 ; Potuganti et al, 2018 ; Liang et al, 2019 ; Rodrigues et al, 2019 ; Donthiboina et al, 2020 ).…”

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.…”

Suzuki–Miyaura Reactions of (4-bromophenyl)-4,6-dichloropyrimidine through Commercially Available Palladium Catalyst: Synthesis, Optimization and Their Structural Aspects Identification through Computational Studies

“…Meanwhile, the arylation of the pyrimidine-substituted bromo-phenyl ring has not been reported so far. Many different methodologies are available for arylation [16,17], while the Suzuki coupling method is the most versatile and frequently used method [18,19], due it its tolerance for moisture by various boronic acids and also by its ability to cover a large number of functional groups [20,21]. Moreover, a number of different catalysts were reported for arylation [22,23].…”