Sonogashira coupling

About: Sonogashira coupling is a research topic. Over the lifetime, 4842 publications have been published within this topic receiving 106816 citations.

The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry†

Abstract: 3.7. Palladium Nanoparticles as Catalysts 888 3.8. Other Transition-Metal Complexes 888 3.9. Transition-Metal-Free Reactions 889 4. Applications 889 4.1. Alkynylation of Arenes 889 4.2. Alkynylation of Heterocycles 891 4.3. Synthesis of Enynes and Enediynes 894 4.4. Synthesis of Ynones 896 4.5. Synthesis of Carbocyclic Systems 897 4.6. Synthesis of Heterocyclic Systems 898 4.7. Synthesis of Natural Products 903 4.8. Synthesis of Electronic and Electrooptical Molecules 906

Recent advances in Sonogashira reactions

Abstract: The coupling of aryl or vinyl halides with terminal acetylenes catalysed by palladium and other transition metals, commonly termed as Sonogashira cross-coupling reaction, is one of the most important and widely used sp2–sp carbon–carbon bond formation reactions in organic synthesis, frequently employed in the synthesis of natural products, biologically active molecules, heterocycles, molecular electronics, dendrimers and conjugated polymers or nanostructures. This critical review focuses on developments in the Sonogashira reaction achieved in recent years concerning catalysts, reaction conditions and substrates (352 references).

Palladium-based catalytic systems for the synthesis of conjugated enynes by Sonogashira reactions and related alkynylations

Abstract: Conjugated alkynes are recurring building blocks in natural products, a wide range of industrial intermediates, pharmaceuticals and agrochemicals, and molecular materials for optics and electronics. The palladium-catalyzed cross-coupling between sp2-hybridized carbon atoms of aryl, heteroaryl, and vinyl halides with sp-hybridized carbon atoms of terminal acetylenes is one of the most important developments in the field of alkyne chemistry over the past 50 years. The seminal work of the 1970s has initiated an intense search for more general and reliable reaction conditions. The interest in the catalytic activation of demanding substrates, the need to minimize the consumption of depletive resources, and the search for easy access to an increased variety of functionalized enynes has led to the current generations of high-turnover catalysts. This Review gives an overview of the highly efficient palladium catalyst systems for the direct alkynylation of C(sp2) halides with terminal alkynes, both in homogeneous and heterogeneous phases.

Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon-carbon coupling precatalysts: a unifying view.

Abstract: Pd catalysis of C-C bond formations is briefly reviewed from the angle of nanoparticles (NPs) whether they are homogeneous or heterogeneous precatalysts and whether they are intentionally preformed or generated from a Pd derivative such as Pd(OAc)2. The most studied reaction is the Heck coupling of halogenoarenes with olefins that usually proceeds at high temperature (120-160 degrees C). Under such conditions, the PdII precursor is reduced to Pd0, forming PdNPs from which Pd atom leaching, subsequent to oxidative addition of the aryl halide onto the PdNP surface, is the source of very active molecular catalysts. Other C-C coupling reactions (Suzuki, Sonogashira, Stille, Negishi, Hiyama, Corriu-Kumada, Ullmann, and Tsuji-Trost) can also be catalyzed by species produced from preformed PdNPs. For catalysis of these reactions, leaching of active Pd atoms from the PdNPs may also provide a viable molecular mechanistic scheme. Thus, the term "PdNP catalysis of C-C coupling" used in this review refers to this function of PdNPs as precursors of catalytically active Pd species (i.e., the PdNPs are precatalysts of C-C coupling reactions).