2 research outputs found
Sonochemical synthesis of bis(tri-n-butylstannyl) aromatic compounds via Barbier-like reactions
This paper reports a study of the synthesis of aryltri-n-butylstannanes via a sonochemical Barbier reaction of aryl- and heteroaryl bromides with bis(tri-n-butyltin) oxide (2) in THF. Our results demonstrate that, despite previous reports on contrary, the aryltributylstannanes can also be obtained under the same reaction conditions via sonicated reactions between aryl monobromides and tri-nbutyltin chloride (2). A comparative study of the reactions of electrophiles 2 and 3 with bromobenzene, 2-bromopyridin, o- and m-bromoanisole, m-bromotoluene, 9-bromophenthrene, and 9-bromoanthracene, indicates that the corresponding aryl- and heteroaryl-tri-n-butylstannyl derivatives are obtained in about the same yields. Best reaction conditions and the results obtained in the investigation of the sonicated reactions between several aromatic and heteroaromatic dibromides are also reported. It was found that the reactions using 1,2-, 1,3-, and 1,4-dibromobenzenes, 4,40-dibromobiphenyl, 1,4-dibromonaphthalene, 2,5- and 3,5-dibromopyridines, and 2,5-dibromothiophene lead to the corresponding bis(tri-n-butylstannylated) derivatives in many cases in very high yields. Also the excellent results obtained in the sonicated reactions of 1,3,5-tribromobenzene with 2 and 3 are reported.Fil: Gerbino, DarĂo CĂ©sar. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico BahĂa Blanca. Instituto de QuĂmica del Sur; Argentina. Universidad Nacional del Sur; ArgentinaFil: Fidelibus, Pablo Martin. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico BahĂa Blanca. Instituto de QuĂmica del Sur; Argentina. Universidad Nacional del Sur; ArgentinaFil: Mandolesi, Sandra Delia. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico BahĂa Blanca. Instituto de QuĂmica del Sur; Argentina. Universidad Nacional del Sur; ArgentinaFil: Ocampo, Romina Andrea. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico BahĂa Blanca. Instituto de QuĂmica del Sur; Argentina. Universidad Nacional del Sur; ArgentinaFil: Scoccia, Jimena. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico BahĂa Blanca. Instituto de QuĂmica del Sur; Argentina. Universidad Nacional del Sur; ArgentinaFil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico BahĂa Blanca. Instituto de QuĂmica del Sur; Argentina. Universidad Nacional del Sur; Argentin
Stereoselective synthesis of 4-oxo-2,5-dienes and conjugated dienes by Stille cross coupling reactions of vinylstannanes
The palladium-catalyzed cross coupling reactions between trineophylstannylvinyl esters and unsaturated acyl chlorides lead mostly to 4-oxo-2,5-dienes in good yields (60-77%). In some cases homocoupling products are also formed. On the other hand, the Stille reaction of Z-di- and trisubstituted vinyl iodides with trineophylvinylstannanes enables the synthesis of polysubstituted butadienes in moderate to good yields (40-60%).Fil: Fidelibus, Pablo Martin. Universidad Nacional del Sur. Departamento de QuĂmica. Instituto de Investigaciones en QuĂmica Orgánica; Argentina. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - BahĂa Blanca; ArgentinaFil: Gerbino, DarĂo CĂ©sar. Universidad Nacional del Sur. Departamento de QuĂmica. Instituto de Investigaciones en QuĂmica Orgánica; Argentina. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - BahĂa Blanca. Instituto de QuĂmica del Sur. Universidad Nacional del Sur. Departamento de QuĂmica. Instituto de QuĂmica del Sur; ArgentinaFil: Mandolesi, Sandra Delia. Universidad Nacional del Sur. Departamento de QuĂmica. Instituto de Investigaciones en QuĂmica Orgánica; ArgentinaFil: Podestá, Julio Cesar. Universidad Nacional del Sur. Departamento de QuĂmica. Instituto de Investigaciones en QuĂmica Orgánica; Argentina. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - BahĂa Blanca. Instituto de QuĂmica del Sur. Universidad Nacional del Sur. Departamento de QuĂmica. Instituto de QuĂmica del Sur; Argentin