Coupling reaction of organostannanes

Palladium-catalyzed cross-coupling reaction of organostannanes with organic halides, triflates, etc. For the catalytic cycle, see Kumada coupling on page 345. 

Farina, V. New perspectives in the cross-coupling reactions of organostannanes. PureAppi. Chem. 1996, 68, 73-78. 

Shirakawa, E., Yamasaki, K., Hiyama, T. Cross-coupling reaction of organostannanes with aryl halides catalyzed by nickel-triphenylphosphine or nickel-lithium halide complex. Synthesis-Stuttgart 99R, 1544-1549. 

In 2000, Liebeskind and Srogl reported a Pd-catalyzed boronic acid-thioether crosscoupling protocol which was mediated by copper(I)-carboxylate [68]. Recognizing their increased accessibility, this protocol was successfully applied to the Stille-type coupling reactions of organostannanes with heteroaromatic thioethers [69]. Specifically, the Pd-catalyzed reaction of 122 and stannane 123 was promoted by copper(I)-3-methylsalicy-late to provide 124 in excellent yield. 

Scheme 17 Cross-coupling reaction of Ar3BiX2 with organostannanes...

T. Forngren, Y. Andersson, B. Lamm, B. Langstrom, Synthesis of [4-F-18]-1-bromo-4-fluorobenzene and its use in palladium-promoted cross-coupling reactions with organostannanes, Acta Chem. Scand. 52 (1998) 475-479. 

Synthesis of a-fluoro-a,/3-unsaturated ketones via palladium-catalyzed cross-coupling reaction of 1-fluorovinyl halides (79) with organostannanes (80)... 

C. Chen, K. Wilcoxen, C.Q. Fluang, N. Strack, J.R. McCarthy, New methods for the synthesis of fluoro olefins via the palladium catalyzed cross-coupling reaction of 1-fluorovinyl halides with organoboranes and organostannanes, J. Fluor. Chem. 101 (2000) 285-290. 

It was also discovered that aryl and vinyl iodides, bromides, and triflates participated efficiently in cross-coupling reactions with organostannanes when catalyzed by palladlum-on-carbon in the presence of Cu(l) as cocatalyst.1... 

Cross-coupling reactions of iodonium salts with terminal alkynes or organostannanes can also be effectively catalyzed by Cul, MnCl2 4H20, or Ni(acac)2 [56,58,103,104]. 

Saa, J. M. Martorell, G. Garda-Raso, A. Palladium-catalyzed cross-coupling reactions of highly hindered, electron-rich phenol triflates and organostannanes./. Org. Chem. 1992, 57, 678-685. 

Table 15 Cross-coupling reactions of 3-methylthio-1,2,4-triazine with aryl-, hetaryl-, or vinyl-boronio aoids and organostannane oompounds...

Casado and Espinet have proposed an associative mechanism on the basis of kinetic studies on the reaction of organostannane derivatives with isolated tra i-ArPdX(AsPh3)2 complexes. The decomplexation of one ligand by the nucleophile generates a bridged intermediate complex. This latter provides a T-shaped complex, which readily gives the coupling product (Scheme 17). " ... 

---