This coupling of terminal alkynes with aryl or vinyl halides is performed with a palladium catalyst, a copper(I) cocatalyst, and an amine base. Typically, the reaction requires anhydrous and anaerobic conditions, but newer procedures have been developed where these restrictions are not important.
Mechanism of the Sonogashira Coupling
The First Applications of Carbene Ligands in Cross-Couplings of Alkyl Electrophiles: Sonogashira Reactions of Unactivated Alkyl Bromides and Iodides
M. Eckhardt, G. C. Fu, J. Am. Chem. Soc., 2003, 125, 13642-13643.
Sustainable HandaPhos-ppm Palladium Technology for Copper-Free Sonogashira Couplings in Water under Mild Conditions
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Copper- and Ligand-Free Sonogashira Reaction Catalyzed by Pd(0) Nanoparticles at Ambient Conditions under Ultrasound Irradiation
A. R. Gholap, K. Venkatesan, R. Pasricha, T. Daniel, R. J. Lahoti, K. V. Srinivasan, J. Org. Chem., 2005, 70, 4869-4872.
Efficient Palladium-Catalyzed Coupling of Aryl Chlorides and Tosylates with Terminal Alkynes: Use of a Copper Cocatalyst Inhibits the Reaction
D. Gelman, S. L. Buchwald, Angew. Chem. Int. Ed., 2003, 42, 5993-5996.
Diastereodivergent Reductive Cross Coupling of Alkynes through Tandem Catalysis: Z- and E-Selective Hydroarylation of Terminal Alkynes
M. K. Armstrong, M. B. Goodstein, G. Lalic, J. Am. Chem. Soc., 2018, 140, 10233-10241.
One-Pot Synthesis of Diarylalkynes Using Palladium-Catalyzed Sonogashira Reaction and Decarboxylative Coupling of sp Carbon and sp2 Carbon
J. Moon, M. Jeong, H. Nam, J. Ju, J. H. Moon, H. M. Jung, S. Lee, Org. Lett., 2008, 10, 945-948.
Investigation of an Efficient Palladium-Catalyzed C(sp)-C(sp) Cross-Coupling Reaction Using Phosphine-Olefin Ligand: Application and Mechanistic Aspects
W. Shi, Y. Luo, X. Luo, L. Chao, H. Zhang, J. Wang, A. Lei, J. Am. Chem. Soc., 2008, 130, 14713-14720.
Synthesis of Internal Alkynes through an Effective Tandem Elimination-Hydrodebromination-Cross-Coupling of gem-Dibromoalkenes with Halobenzenes
Y. Ji, N. Zhong, Z. Kang, G. Yan, M. Zhao, Synlett, 2018, 29, 209-214.
One-Pot Conversion of Aldehydes and Aryl Halides to Disubstituted Alkynes via Tandem Seyferth-Gilbert Homologation/Copper-Free Sonogashira Coupling
A. Sapegin, M. Krasavin, J. Org. Chem., 2019, 84, 8788-8795.
General, Robust, and Stereocomplementary Preparation of β-Ketoester Enol Tosylates as Cross-Coupling Partners Utilizing TsCl-N-Methylimidazole Agents
H. Nakatsuji, K. Ueno, T. Misaki, Y. Tanabe, Org. Lett., 2008, 10, 2131-2134.
Single-Isomer Tetrasubstituted Olefins from Regioselective and Stereospecific Palladium-Catalyzed Coupling of β-Chloro-α-iodo-α,β-unsaturated Esters
A. B. Lemay, K. S. Vulic, W. W. Ogilvie, J. Org. Chem., 2006, 71, 3615-3618.
Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides Using Near Stoichiometric Carbon Monoxide
K. T. Neumann, S. R. Laursen, A. T. Lindhardt, B. Bang-Andersen, T. Skrydstrup, Org. Lett., 2014, 16, 2216-2219.