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Tandem reduction and trifluoroethylation of quinolines and quinoxalines with trifluoroacetic acid and trimethylamine borane†
Yi-Na Li,Ming-Xi Zhou,Jin-Bo Wu,Zhen Wang,Yao-Fu Zeng
Organic & Biomolecular Chemistry Pub Date : 11/24/2022 00:00:00 , DOI:10.1039/D2OB01923J
Abstract

A metal-free tandem reduction and N-trifluoroethylation of quinolines and quinoxalines has been developed. It provided a convenient route to access trifluoroethylated tetrahydroquinolines and tetrahydroquinoxalines. This one-pot method avoids the purification process of the intermediate. Mechanistically, the in situ-generated boryl acetal species reacted with tetrahydroquinolines to generate iminiums followed by reduction to give the target compounds.

Graphical abstract: Tandem reduction and trifluoroethylation of quinolines and quinoxalines with trifluoroacetic acid and trimethylamine borane
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