Sonogashira Negishi coupling reaction

In 2011, Lipshutz s team reported the successful application of the amphiphile TPGS-750-M for the realization of Sonogashira-Hagihara coupling reactions (as well as Heck-Mizoroki, Suzuki-Miyaura, Buchwald-Hartwig, Negishi-like couplings, C-H activation reactions, and so on... 

Dichloro- and 3,5-dibromoisothiazole-4-carbonitriles 285a/b undergo regioselective Stille, Negishi, Sonogashira coupling reactions at C-5 to provide 3-halo-5-substituted... 

Although 2,5-dibromopyridine may be regiospecifically lithiated at C(5) [149], Pd-catalyzed couplings, including the Sonogashira, Negishi [150], and alkoxycarbonylation reactions [151] all preferentially occur at the C(2) position, as illustrated by the formation of 190. 

For a listing of earlier reviews of the Negishi, Suzuki, Stifle, Sonogashira and other Pd-catalyzed cross-coupling reactions, see E. Negishi, in Chap. III.l of Reference 1, pp. 215-227. 

The chlorotetrazines were found to react not only under regular Sonogashira coupling conditions, but also in the presence of zinc acetylides. This reaction is an extension of the Negishi coupling, which sometimes... 

These include couplings such as the Kumada, Sonogashira, Negishi, and Stille reactions. 

Palladium-catalyzed coupling reactions of 2-(5-iodoisoxazol-3-yl)pyridine 274 with a variety of organometallic compounds led to derivatives 275-278 through Sonogashira, Suzuki, Negishi, and Stille reactions, respectively (Scheme 64) <20010L4185>. 

The discovery, use, and further development of cross-coupling reactions have mightily advanced the field of organic synthesis. Today, chemists routinely use Stille, Suzuki, Sonogashira, and Negishi reactions to construct new C-C bonds, and this step is often the key to successful synthesis of incredibly complex... 

As with the Negishi and Suzuki reactions, the same solid-support (vide supra) could be adapted to the Sonogashira reaction [62]. The solid-supported bromopyridine 178 could undergo cross-coupling reactions with a variety of alkynes and be released from the solid-support to allow isolation of 331. 

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