377. | Sonogashira Coupling (Sonogashira-Hagihara Coupling) K. Sonogashira et al., Tetrahedron Lett. 16, 4467 (1975). Palladium(0)-copper(I) catalyzed cross-coupling between sp2-hybridized organic halides and terminal acetylenes. Synthetic applications: A. S. Karpov et al., J. Org. Chem. 68, 1503 (2003); M. Erdélyi, A. Gogoll, ibid. 6431; A. Elangovan et al., Org. Lett. 5, 1841 (2003); M. S. M. Ahmed, A. Mori, ibid. 3057; M. Eckhardt, G. C. Fu, J. Am. Chem. Soc. 125, 13642 (2003); E. Mas-Marzá et al., Tetrahedron Lett. 44, 6595 (2003). Nickel catalyzed reaction: I. P. Beletskaya et al., ibid. 5011. Copper-free modifications: A. Soheili et al., Org. Lett. 5, 4191 (2003); L. Djakovitch, P. Rollet, Adv. Synth. Catal. 346, 1782 (2004). Reviews: K. Sonogashira, J. Organomet. Chem. 653, 46-49 (2002); R. R. Tykwinski, Angew. Chem. Int. Ed. 42, 1566-1568 (2003). |