Issue 20, 2024

A sustainable strategic approach for N-alkylation of amines with activation of alcohols triggered via a hydrogen auto-transfer reaction using a Pd(ii) complex: evidence for metal–ligand cooperativity

Abstract

This work describes a new well-defined, air-stable, phosphine free palladium(II) [Pd(L)Cl] (1) catalyst. This catalyst was utilized for N-alkylation of amines and indole synthesis where H2O was found to be the by-product. A broad range of aromatic amines were alkylated using this homogeneous catalyst with a catalyst loading of 0.1 mol%. Greener aromatic and aliphatic primary alcohols were utilized and a hydrogen auto-transfer strategy via a metal–ligand cooperative approach was investigated. The precursor of the antihistamine-containing drug molecule tripelennamine was synthesized on a gram scale for large-scale applicability of the current synthetic methodology. A number of control experiments were performed to investigate the possible reaction pathway and the outcomes of these experiments indicated the azo-chromophore as a hydrogen reservoir during the catalytic cycle.

Graphical abstract: A sustainable strategic approach for N-alkylation of amines with activation of alcohols triggered via a hydrogen auto-transfer reaction using a Pd(ii) complex: evidence for metal–ligand cooperativity

Supplementary files

Article information

Article type
Paper
Submitted
26 Mar 2024
Accepted
22 Apr 2024
First published
23 Apr 2024

Dalton Trans., 2024,53, 8740-8749

A sustainable strategic approach for N-alkylation of amines with activation of alcohols triggered via a hydrogen auto-transfer reaction using a Pd(II) complex: evidence for metal–ligand cooperativity

V. Kumar Chaudhary, P. Kukreti, K. Sharma, K. Kumar, S. Singh, S. Kumari and K. Ghosh, Dalton Trans., 2024, 53, 8740 DOI: 10.1039/D4DT00864B

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