Triple role of boronic acid as a catalyst in the alkylation of quinoline to functionalized tetrahydroquinoline

Abstract

The triple role of arylboronic acid as a catalyst in the alkylation of quinoline to N-substituted tetrahydroquinoline with a diaryl motif at the C6-position has been developed. This reaction involves the tandem reduction of quinoline to tetrahydroquinoline, followed by reductive N-alkylation with aldehyde to form N-alkylated tetrahydroquinoline and subsequent regioselective alkylation at the C6-position using para-quinone methides (p-QMs) in a one-pot operation. The methodology is compatible with a wide variety of functional groups and is also useful in the late-stage functionalization of pharmaceuticals. The mechanistic study demonstrates the existence of organoboron catalysts as both Lewis acids and hydrogen-bond donors.

Graphical abstract: Triple role of boronic acid as a catalyst in the alkylation of quinoline to functionalized tetrahydroquinoline

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Article information

Article type
Paper
Submitted
29 May 2025
Accepted
23 Jun 2025
First published
24 Jun 2025

Org. Biomol. Chem., 2025, Advance Article

Triple role of boronic acid as a catalyst in the alkylation of quinoline to functionalized tetrahydroquinoline

S. K. Senapati, A. Borah, S. Hazarika and A. Das, Org. Biomol. Chem., 2025, Advance Article , DOI: 10.1039/D5OB00895F

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