Reductive N-Arylethylation of Aromatic Amines and N-Heterocycles with Enol Ethers

Abstract

A convenient method for N-arylethylation of aromatic amines and heterocycles under mild reductive conditions was developed using (2-methoxyvinyl)(hetero)arenes as building blocks and triethylsilane/trifluoroacetic acid as reducing agent. This protocol is compatible with numerous functional groups, and aliphatic amines are inert due to protonation.

Copper-Catalyzed Regio- and Stereoselective Three-Component Coupling of Allenyl Ethers with gem-Dichlorocyclobutenones and B2pin2

“…The carbonyl group of 8 could be converted to a hydroxy group in the presence of the equivalents of n BuLi and NaBH 4 ( 9 and 10 ). Next, the reductive arylethylation of aromatic amine with enol ether was carried out to form compound 11 in the presence of the equivalents of TFA and Et 3 SiH . Additionally, cyclobutenone 8 could be engaged in a Wittig reaction to generate the desired product 12 in 92% yield .…”