820250-70-2Relevant academic research and scientific papers
Nickel-catalyzed acylstannylation and alkynylstannylation of 1,2-dienes
Nakao, Yoshiaki,Shirakawa, Eiji,Tsuchimoto, Teruhisa,Hiyama, Tamejiro
, p. 3701 - 3721 (2007/10/03)
Carbostannylation of 1,2-dienes using acyl- and alkynylstannanes was achieved by means of nickel catalysis. In particular, acylstannylation of 1,2-dienes could be carried out with bis(1,5-cyclooctadiene)nickel [Ni(cod) 2] and acylstannanes to give selectively α-acylmethyl(vinyl) stannanes. The reaction was also applicable to acylstannanes prepared in situ by protonolysis of α-alkoxyalkenylstannanes or by reactions of α-silyloxyvinylstannanes with aldehyde acetals. For alkynylstannylation, a combination of Ni(cod)2 and 1,3-bis(diphenylphosphino)propane (dppp) was found to be effective to afford α-alkynylmethyl(vinyl)stannanes, whereas the Ni(cod)2-1,3-bis(dimethylphosphino)propane (dmpp) catalyst switched the regioselectivity to give (Z)-α- alkynylmethyl(alkenyl)stannanes. The acylstannylation products were successfully converted into various conjugated or unconjugated enones by a combination of cross-coupling and NaH-catalyzed isomerization. The alkynylstannylation products were transformed by cross- or homo-coupling reactions to various enynes or 2,3-bis(alkynylmethyl)-1,3-dienes, versatile precursors for variously substituted polycyclic compounds.
Synthesis of functionalized alkenes by transition metal-catalyzed carbostannylations of alkynes and dienes followed by cross-coupling reactions
Shirakawa, Eiji,Hiyama, Tamejiro
, p. 114 - 121 (2007/10/03)
Transition metal-catalyzed carbostannylation of alkynes and 1,2-dienes provides alkenylstannanes having an alkynyl, alkenyl or acyl group with or without conjugation. The alkenylstannanes are transformed to various unsaturated compounds with diverse funct
Transition metal-catalyzed carbostannylation of alkynes and dienes
Shirakawa, Eiji,Hiyama, Tamejiro
, p. 1435 - 1450 (2007/10/03)
Carbon-tin bonds in alkynyl-, allyl-, acyl-, alkenyl-, and arylstannanes were found to add to carbon-carbon unsaturated bonds of alkynes, 1,3-dienes and 1,2-dienes in the presence of a catalytic amount of palladium or nickel complexes to give alkenyl- or
