Issue 12, 2024

Ruthenium catalyzed dehydrogenative α-C–H functionalization of β-naphthol using alcohols: a metal–ligand cooperative borrowing hydrogen approach

Abstract

Chemoselective α-C–H functionalization of β-naphthol is achieved with inexpensive and readily available alcohols using a well-defined, air-stable, and easy-to-prepare Ru(II)-catalyst (1a) bearing a redox-active tridentate pincer (L1a). Only 1.0 mol% of 1a showed promising catalytic efficiency, producing various α-alkylated β-naphthols in moderate to good isolated yields starting from different aromatic, hetero-aromatic, and aliphatic alcohols, including methanol, ethanol, and other long-chain alcohols. 1a also efficiently catalyzes the α-C–H alkylation of β-naphthols using aromatic diols as the di-alkylating agent. 1a also exhibited promising results during the large-scale synthesis of α-alkylated β-naphthols. Mechanistic investigation revealed that the 1a-catalyzed α-C–H functionalization of β-naphthol proceeds via a borrowing hydrogen path where hydrogen is transferred from alcohol to the azo-chromophore of the tridentate pincer via a transient ruthenium hydride intermediate, which was transferred in the later stage to the in situ formed alkylidenenaphthalen-2(1H)-one intermediate, producing α-alkylated β-naphthols as the final product.

Graphical abstract: Ruthenium catalyzed dehydrogenative α-C–H functionalization of β-naphthol using alcohols: a metal–ligand cooperative borrowing hydrogen approach

Supplementary files

Article information

Article type
Paper
Submitted
03 Apr 2024
Accepted
12 May 2024
First published
13 May 2024

Catal. Sci. Technol., 2024,14, 3540-3549

Ruthenium catalyzed dehydrogenative α-C–H functionalization of β-naphthol using alcohols: a metal–ligand cooperative borrowing hydrogen approach

A. K. Guin, S. Chakraborty, S. Khanra, A. S. Mohapatra and N. D. Paul, Catal. Sci. Technol., 2024, 14, 3540 DOI: 10.1039/D4CY00434E

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