Walid Al-Maksoud

Publications (3)1.02 Total impact

• Article: Direct palladium/copper oxidative cross-coupling of α-methylstyrene with acrylates

  Walid Al-Maksoud, Laurent Djakovitch, Mohamad Jahjah, Catherine Pinel
  [show abstract] [hide abstract]
  ABSTRACT: Fully palladium/copper catalytic oxidative cross-coupling of acrylates with α-methylstyrene was performed in a DMSO/AcOH (1:1) mixture at 60 °C in the air. This improves previous procedures which employed stoichiometric amounts of copper and oxygen. Thus various acrylates were effectively coupled to α-methylstyrene giving the expected compounds in moderate to good yields (44%–65%) as a mixture of E and Z isomers. Keywordsdirect cross-coupling-oxidative couplings-palladium-copper-catalytic procedures-olefin cross-coupling
  Science China-Chemistry 04/2012; 53(9):1927-1931. · 1.02 Impact Factor
• Article: Synthesis of diethyl 2-(aryl)vinylphosphonate by the Heck reaction catalysed by supported palladium catalysts

  Jinane Tarabay, Walid Al-Maksoud, Farouk Jaber, Catherine Pinel, Swamy Prakash, Laurent Djakovitch
  [show abstract] [hide abstract]
  ABSTRACT: The synthesis of diethyl 2-(aryl)vinylphosphonate through direct Heck coupling reaction of the diethyl vinylphosphonate with aryl or heteroaryl halides catalysed by solid materials ([Pd(NH3)4]/NaY, Pd/C, PdO/SiO2) is reported. After optimising the reaction conditions (1.3 mol% [Pd(NH3)4]/NaY, DMF, K2CO3, 110-140 °C), various aryl and heteroaryl halides were engaged in this reaction leading in all cases good to high yields. Interestingly, when using activated aryl bromides the palladium loading could be lowered to only 0.25 mol%. While highly active when coupling aryl iodides (i.e. only 0.15 mol% required), the PdO/SiO2 catalyst was found to be inactive when considering aryl bromides. Deep study of this catalytic material revealed that in the case of aryl bromides, absence of in situ reduction of the catalyst precursor prevents the cross-coupling reaction with this latter material.
  Applied Catalysis A: General. 01/2010; 388(1-2):124-133.
• Article: Synthesis of diethyl 2-(aryl)vinylphosphonates by the Heck reaction catalysed by well-defined palladium complexes

  Walid Al-Maksoud, Julien Mesnager, Farouk Jaber, Catherine Pinel, Laurent Djakovitch
  [show abstract] [hide abstract]
  ABSTRACT: Pd-catalysed procedures for the direct Heck arylation of diethyl vinylphosphonate with various aryl or heteroaryl halides toward the synthesis of diethyl 2-(aryl)vinylphosphonates are reported. Several homogeneous catalytic systems (i.e. Herrmann palladacycle, Nolan (NHC)-palladium catalyst, Pd(OAc)2/PPh3) were used and compared within the study. High conversions and selectivities were achieved under optimised conditions (2 mol% [Pd], NMP, K2CO3, 140 °C) whatever the homogeneous catalyst used.
  Journal of Organometallic Chemistry. 01/2009; 694(20):3222-3231.