Efficient palladium-catalyzed nucleophilic addition of triorganoindium reagents to carbocyclic derivatives
Palladium (0)-catalyzed allylic substitution reactions employing triorganoindium reagents have been investigated. In situ generated vinyl- and arylindiums react with substituted and unsubstituted cyclohex-2-enyl esters in the presence of 1-3 mol % Pd2(dba)3 to produce vinyl- or arylcyclohexenes in moderate to excellent yields. The stereoselectivity of this process was also examined, and evidence is presented that the reaction proceeds with inversion of stereochemical configuration.
Baker, Lucas,Minehan, Thomas
p. 3957 - 3960
(2007/10/03)
Palladium-catalyzed reaction of boronic acids with chiral and racemic α-bromo sulfoxides
Palladium-catalyzed cross-coupling reactions of racemic α-bromo sulfoxides with boronic acids are carried out in either aqueous or nonaqueous medium with formation of a new C sp3-C sp2 bond. The arylation of chiral α-bromo sulfoxides occurs without racemization. The cross-coupling reaction is general and gives high yields with arylboronic acids substituted with either donor or acceptor groups but gives poor results with heteroarylboronic acids. The best yields are obtained using degassed solvents and CsF instead of aqueous base. The use of aqueous base and the presence of oxygen favor the homocoupling side reaction.
Rodriguez, Nuria,Cuenca, Ana,Ramirez De Arellano, Carmen,Medio-Simon, Mercedes,Peine, Denissa,Asensio, Gregorio
p. 8070 - 8076
(2007/10/03)
Homocoupling of aryl iodides and bromides promoted by sulfur-containing palladacycles
Sulfur-containing palladacycles, in particular those derived from the orthometalation of benzylthioethers, effectively promote the homocoupling of aryl iodides and bromides, under relatively mild reaction conditions to furnish symmetrical biphenyls in good yields.
Silveira, Priscila B.,Lando, Vanusa R.,Dupont, Jairton,Monteiro, Adriano L.
p. 2327 - 2329
(2007/10/03)
Extension of the Heck reaction to the arylation of activated thiophenes
The direct arylation of activated thiophenes was accomplished in moderate to good yields using a Heck-type reaction with the mixture of Pd(OAc)2 and n-Bu4NBr as a catalytic system. This new arylation method is applied to different derivatives and has proved to be compatible with sensitive functional groups. Furthermore, the substituent nature and position on the thiophene moiety influence the cross coupling. In particular the substitution is regiospecific when the heterocycle is substituted at position 2 with an electron withdrawing group.
Lavenot,Gozzi,Ilg,Orlova,Penalva,Lemaire
p. 49 - 55
(2007/10/03)
Activation of Reducing Agents. Sodium Hydride Containing Complex Reducing Agents. 32. NiCRAL's as Very Efficient Agents in Promoting Cross-Coupling of Aryl Halides
Nickel-containing complex reducing agents NiCRA-bpy are shown to be the first nickel reagents able to efficiently perform cross-coupling of aryl halides.The presence of KI in the reaction medium generally improves the procedure.The mechanism and influence of the structures of the substrates are discused.
Lourak, Mouhsine,Vanderesse, Regis,Fort, Yves,Caubere, Paul