Pd-mBDPP-catalyzed regioselective internal arylation of electron-rich olefins by aryl halides.
meso-2,4-Bis(diphenylphosphino)pentane (mBDPP) has proved to be an effective regiocontrolling ligand for palladium-catalyzed internal arylation by aryl bromides of electron-rich olefins in a common solvent DMSO with no need for any halide scavengers. The arylation of the benchmark electron-rich olefin butyl vinyl ether took place smoothly to afford exclusively alpha-arylated product with high isolated yields. The better performance of mBDPP, compared with that of the commonly used DPPP [1,3-bis(diphenylphosphino)propane], highlights the important but subtle effect of ligand on the regioselectivity of the Heck arylation reactions.
Liu
Shifang
S
Department of Chemistry, Liverpool Centre for Materials and Catalysis, University of Liverpool, Liverpool L697ZD, UK.
Berry
Neil
N
Thomson
Nick
N
Pettman
Alan
A
Hyder
Zeynab
Z
Mo
Jun
J
Xiao
Jianliang
J
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D010420:Pentanes / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry
C470607:2,4-bis(diphenylphosphino)pentane; D000475:Alkenes; D004987:Ethers; D006842:Hydrocarbons, Brominated; D006846:Hydrocarbons, Halogenated; D009281:Naphthalenes; D010420:Pentanes; D010720:Phosphines; D014753:Vinyl Compounds; C031721:naphthalene; C096129:n-butyl vinyl ether; D010165:Palladium