Cross-coupling of organostannane with

Since its introduction by Allred and Liebsekind in 1996 [114], copper thiophene-2-carboxylate (CuTC) has emerged as a mild and useful reagent for mediating the cross-coupling of organostannanes with vinyl iodides at room temperature. CuTC is especially effective for substrates that are not stable at high temperature. In Paterson s total synthesis of elaiolide, he enlisted a CuTC-promoted Stille cyclodimerization of vinyl iodide 131 to afford the 16-membered macrocycle 132 under very mild conditions [115]. 

Allred, G. D., Liebeskind, L. S. Copper-Mediated Cross-Coupling of Organostannanes with Organic Iodides at or below Room Temperature. J. Am. Chem. Soc. 1996,118, 2748-2749. 

Kang, S. K., Kim, J. S., Choi, S. C. Copper- and manganese-catalyzed cross-coupling of organostannanes with organic iodides in the presence of sodium chloride. J. Org. Chem. 1997, 62, 4208-4209. 

The Stille reaction involves the transition-metal-mediated cross-coupling of organostannanes with organic electrophiles. Generally, it is a mild and efficient way for the creation of C—C bonds, especially between Csp or Csp centers. The most significant disadvantage of the method is... 

Cross-couplings. The Stille coupling of organostannanes with hypervalent iodine compounds has a broad scope. Diaryl and dialkenyl tellurides are also active toward alkenes if the catalytic system contains AgOAc. ... 

Scheme 1.262). Palladium-catalyzed cross-coupling of 977 with a variety of organostannanes then afforded the 4-substituted oxazoles 202 and 978a-c in excellent yield. 

The late Professor J. K. Stille pioneered the development of a very effective and versatile palladium-mediated C-C bond forming method - the palladium-catalyzed cross-coupling of organic electrophiles with organostannanes.48 This process continues to enjoy much success in organic synthesis because it proceeds in high yields under mild reaction conditions and because it tolerates a... 

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

Palladium- and copper-catalysed cross-coupling of organotellurium dichlorides with organostannanes and organoboronic acids... 

In 2001, Nolan described the palladium/imidazoilium salt-catalyzed coupling of aryl halides with hypervalent organostannanes.The imidazolium salt 36 in combination with Pd(OAc)2 and TBAF was found to be most effective for the cross-coupling of aryl bromides and electron-deficient aryl chlorides with aryl and vinyl stannanes. 

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. 

Oxidative addition to Pd(0) is an important step in many C—C bond-forming reactions catalyzed by Pd. These include the cross-coupling of vinyl or aryl halides or triflates with Grignard reagents or organostannanes ... 

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