Palladium-catalyzed Stille couplings

Rai, R. Aubrecht, K. B. Collum, D. B. Palladium-catalyzed Stille couplings of aryl-, vinyl-, and alkyltrichlorostannanes in aqueous solution. Tetrahedron Lett. 1995, 36, 3111—3114. 

Hoshino M, Degenkolb P, Curran DP, Palladium catalyzed Stille couplings with fluorous tin reactants, J. Org. Chem., 62 8341-8349, 1997. 

Homolytic photocleavage of the C-S bond of benzyl sulfide [58, 59] has been adapted for use in linkers for solid-phase organic reactions. Cleavage was substrate-dependent photolytic scission of site b happened only to structures such as 37, which contain a biphenyl group. Trimethylphenyltin 36 underwent a palladium-catalyzed Stille coupling with the resin-bound aryl iodide 35 to give, after photolysis, a biphenyl (Scheme 17.19). 

Guanine and guanosine are, of course, commercially available and can be derivatized in numerous ways. Along these lines, Sessler has used [32] a palladium-catalyzed Stille coupling to connect a porphyrin system to 8-bromoguanosine for use in a self-assembling, photosynthetic model system... 

Li, X.Z., Y. Zhang, R.Q. Yang, J. Huang, W. Yang, and Y. Cao. 2005. Novel saturated red-emitting poly(p-phenylenevinylene) copolymers with narrow-band-gap units of 2,1,3-benzothiadiazole synthesized by a palladium-catalyzed stille coupling reaction. / Polym Sci Part A Polym Chem 43 (11) 2325-2336. 

The first example of a palladium-catalyzed Stille couplings of a nonheteroaryl chloride was provided by Migita, who established that [Pd(PPh3)4] catalyzes the... 

For examples of (t -chloroarene)chromium tricarbonyl complexes participating in palladium-catalyzed Stille couplings, see (a) Scott,... 

Despite the drawback of using tin reagents, the palladium-catalyzed Stille coupling provides a powerful pathway for C-C bond formation. Nowadays, numerous applications exist for organic synthesis. Nevertheless, the toxicity of the tin compounds limits their application on a larger scale [45]. 

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