102775-25-7Relevant academic research and scientific papers
Synthesis and Functionalization of Allenes by Direct Pd-Catalyzed Organolithium Cross-Coupling
Casti?eira Reis, Marta,Feringa, Ben L.,Mateos-Gil, Jaime,Mondal, Anirban
, p. 7823 - 7829 (2020)
A palladium-catalyzed cross-coupling between in situ generated allenyl/propargyl-lithium species and aryl bromides to yield highly functionalized allenes is reported. The direct and selective formation of allenic products preventing the corresponding isomeric propargylic product is accomplished by the choice of SPhos or XPhos based Pd catalysts. The methodology avoids the prior transmetalation to other transition metals or reverse approaches that required prefunctionalization of substrates with leaving groups, resulting in a fast and efficient approach for the synthesis of tri- and tetrasubstituted allenes. Experimental and theoretical studies on the mechanism show catalyst control of selectivity in this allene formation.
METAL CATALYSIS IN ORGANIC REACTIONS. 17. A NICKEL-PROMOTED ROUTE TO SUBSTITUTED ALLENES BY REACTION OF 1-BROMO-1,2-DIENES WITH ALKYL METALS.
Caporusso, Anna Maria,Settimo, Federico Da,Lardicci, Luciano
, p. 5101 - 5104 (1985)
Nickel complexes are found to be catalytically active in the cross-coupling reactions of allenic bromides with alkyl metals to give substituted allenes in excellent yields.The catalytic process proceeds generally with inversion of configuration in the allenyl moiety.
Selective synthesis of allenes and alkynes through ligand-controlled, palladium-catalyzed decarboxylative hydrogenolysis of propargylic formates
Ohmiya, Hirohisa,Yang, Mingyu,Yamauchi, Yoshihiro,Ohtsuka, Yuhki,Sawamura, Masaya
supporting information; experimental part, p. 1796 - 1799 (2010/09/07)
Ligand-controlled regioselective palladium-catalyzed decarboxylative hydrogenolysis of propargylic formates is described. A wide range of allenes and alkynes were obtained by using either 1,2-diphenylphosphinoethane (DPPE) or 1,6-bisdiphenylphosphinohexane (DPPH) as a catalyst ligand.
REACTIONS OF 3-ALKYL- AND 3,3-DIALKYL-1-BROMOALLENES WITH ORGANOCUPRATES: EFFECTS OF THE NATURE OF THE CUPRATE REAGENT ON THE REGIO- AND STEREOSELECTIVITY
Caporusso, Anna Maria,Polizzi, Carmela,Lardicci, Luciano
, p. 6073 - 6076 (2007/10/02)
Organocuprates induce 1,3- and direct substitution in 3-alkyl- and 3,3-dialkyl-1-bromo-1,2-dienes leading respectively to either terminal acetylenes or allenic hydrocarbons.The nature of the cuprate exerts a prominent role in determining both the regio- and the stereochemistry of these reactions.
