Reductive Alkylation of Quinolines to N-Alkyl Tetrahydroquinolines Catalyzed by Arylboronic Acid
Organic Letters, 2021•ACS Publications
A boronic acid catalyzed one-pot tandem reduction of quinolines to tetrahydroquinolines
followed by reductive alkylation by the aldehyde has been demonstrated. This step-
economcial synthesis of N-alkyl tetrahydroquinolines has been achieved directly from
readily available quinolines, aldehydes, and Hantzsch ester under mild reaction conditions.
The mechanistic study demonstrates the unique behavior of organoboron catalysts as both
Lewis acids and hydrogen-bond donors.
followed by reductive alkylation by the aldehyde has been demonstrated. This step-
economcial synthesis of N-alkyl tetrahydroquinolines has been achieved directly from
readily available quinolines, aldehydes, and Hantzsch ester under mild reaction conditions.
The mechanistic study demonstrates the unique behavior of organoboron catalysts as both
Lewis acids and hydrogen-bond donors.
A boronic acid catalyzed one-pot tandem reduction of quinolines to tetrahydroquinolines followed by reductive alkylation by the aldehyde has been demonstrated. This step-economcial synthesis of N-alkyl tetrahydroquinolines has been achieved directly from readily available quinolines, aldehydes, and Hantzsch ester under mild reaction conditions. The mechanistic study demonstrates the unique behavior of organoboron catalysts as both Lewis acids and hydrogen-bond donors.
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