Nickel-catalyzed asymmetric ring opening of oxabenzonorbornadienes with arylboronic acids.
A new, versatile, and highly efficient nickel-catalyzed asymmetric ring-opening (ARO) reaction of oxabenzonorbornadienes with a wide variety of arylboronic acids has been developed, yielding cis-2-aryl-1,2-dihydronaphthalen-1-ols in high yields (up to 99%) with good to excellent enantioselectivities (up to 99% ee) under very mild conditions. The effects of various nickel precursors, chiral bidentate ligands, catalyst loadings, bases, solvents, and temperatures on the yield and enantioselectivity of the reaction were also investigated. A plausible mechanism was proposed to account for the formation of the corresponding cis-ring-opened products based on the X-ray structure of product 4b.
Guangzhou Key Laboratory of Materials for Energy Conversion and Storage; School of Chemistry and Environment, South China Normal University , Guangzhou 510006, People's Republic of China.
Zhongyi
Z
Zeng
Dingqiao
D
Yang
Yuhua
Y
Long
Xuejing
X
Pan
Guobao
G
Huang
Xiongjun
X
Zuo
Wen
W
Zhou
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009636:Norbornanes / Q000737:chemistry*; D013237:Stereoisomerism
D001897:Boronic Acids; D009636:Norbornanes; D009532:Nickel