Journal
RSC ADVANCES
Volume 11, Issue 2, Pages 909-917Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ra09601f
Keywords
-
Categories
Ask authors/readers for more resources
The palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-2-ylmethyl acetate with N, S, O and C soft nucleophiles was investigated, showing different catalytic systems have significant effects on the reaction outcome, with nucleophilic substitution only occurring at the benzylic position.
The palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-2-ylmethyl acetate with N, S, O and C soft nucleophiles has been investigated. The success of the reaction is dramatically influenced by the choice of catalytic system: with nitrogen based nucleophiles the reaction works well with Pd-2(dba)(3)/dppf, while with sulfur, oxygen and carbo-nucleophiles [Pd(eta(3)-C3H5)Cl](2)/XPhos is more efficient. The regiochemical outcome shows that the nucleophilic substitution occurs only on the benzylic position of the eta(3)-(benzofuryl)methyl complex. The high to excellent yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2-substituted benzo[b]furans.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available