An Efficient Mesoporous Cu‐Organic Nanorod for Friedländer Synthesis of Quinoline and Click Reactions

TL;DR: In this paper, a triazine functional hierarchical mesoporous organic polymer (HMOP) with nanorod morphology together with large BET surface area ∼1218m2m2g−1, huge pore volume and dual micro/mesopore architectures was presented.

Abstract: Within the green chemistry context, heterogeneous catalysis for the synthesis of N‐heterocycles from renewable resources using non‐precious metals has garnered great interest in terms of economic and environmental perspectives. Herein, we present a triazine functional hierarchical mesoporous organic polymer (HMOP) with nanorod morphology together with large BET surface area ∼1218 m2 g−1, huge pore volume&γτ“;6 mL g−1 and dual micro/mesopore architectures. Subsequent Cu‐coordination with nitrogen atoms of the HMOP provides a robust catalyst (Cu‐HMOP) to accomplish multi‐step cascade reactions for preparation of N‐heterocycles by different routes. For instance, the Cu‐HMOP efficiently catalyzes one‐pot sequential multi‐step oxidative dehydrogenative coupling of 2‐aminobenzyl alcohol with diverse aromatic ketones to afford corresponding quinolines in excellent isolated yields (up to 97 %). Secondly, the present catalyst exhibits good aerobic oxidative dehydrogenation activity of amines to imines. Thirdly, for “click” reaction involving azides‐alkynes, the Cu‐HMOP produced quantitative yield for 1,4‐disubstituted 1,2,3‐triazole derivatives at room temperature using water as solvent. Verification of active metal leaching by a hot filtration test as well as reusability of the retrieved Cu‐HMOP catalysts shows a consistent activity in the multi‐component quinoline synthesis as model reaction.