N,N′‑Bisaryl
Substituted Chiral Linker-Bridged Bis(N‑Heterocyclic
Carbene) Palladium Complexes: Design, Synthesis, and Catalytic Properties
Posted on 2017-03-24 - 12:48
A series of novel N,N′-bisaryl
bis(NHC) (NHC = N-heterocyclic carbene) precursors 5a–e, 12a–d, and 13a–c and their palladium
complexes 14a–e, 15a–d, and 16a,b with
(1R,2R)-cyclohexene and (1R,2R)-diphenylethylene linkers have been
designed, synthesized in good yields, and fully characterized by NMR,
HRMS, and elemental analysis. The X-ray single crystal analysis of 15a showed that these complexes adopted a slightly distorted
square-planar geometry around the Pd(II) center. These N,N′-bisaryl-bis(NHC)-Pd complexes exhibit
excellent catalytic activity in asymmetric aryl–aryl cross-coupling
reactions of arylboronic acids and aryl halides. The axial chiral
biaryl compounds could be achieved in high yields (up to 74%) and
good enantioselectivities (up to 60% ee) within 24 h. The results
show that for this kind of bis(NHC) palladium catalysts the structure
characteristics of the chiral linkers have decisive effect on the
enantioselectivities of cross-coupling reactions.
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Tang, Junkai; He, Yu; Yu, Jianfeng; Zhang, Dao (2017). N,N′‑Bisaryl
Substituted Chiral Linker-Bridged Bis(N‑Heterocyclic
Carbene) Palladium Complexes: Design, Synthesis, and Catalytic Properties. ACS Publications. Collection. https://doi.org/10.1021/acs.organomet.7b00092
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AUTHORS (4)
JT
Junkai Tang
YH
Yu He
JY
Jianfeng Yu
DZ
Dao Zhang
KEYWORDS
results showchiral biaryl compoundschiral linkersaryl halidesNMRyield24 harylboronic acidspalladium complexes 14square-planar geometrycross-coupling reactionsenantioselectivitiestructure characteristicsCatalytic Propertiesprecursors 5heterocyclic carbenenovel NNHCPalladium Complexescrystal analysisHRMS