Palladium-catalyzed carbostannylation by means of reagents containing carbon-tin-halogen inter-element linkages

Reagents containing carbon-tin-halogen inter-element linkages were effectiv e for palladium-catalyzed carbostannylation. In situ generated allyltin tri chlorides add to carbon-carbon double bonds of bicyclo[2.2.1]hept-2-ene (no rbornene) and bicyclo[2.2.1]hepta-2,5-diene (norbornadiene), stereoselectiv ely, under the catalysis of palladium(0) species in good yields. The regios electivity of unsymmetrically substituted allylic reagents dramatically alt ers with the choice of the tin(II) salt. Aryltin trichlorides undergo palla dium-catalyzed arylstannylation of norbornene, giving a mixture of products composed of that taking one norbornene and that taking two norbornenes. Th e product ratio is dependent on the choice of the solvent and electronic na ture of the aromatic substituent. (C) 2000 Elsevier Science S.A. All rights reserved.