Sustainable production of triazoles from lignin major motifs

Author:

Zhu Wenqing12,Shi Yue3,Lu Jinfei1,Han Fengan1,Luo Wenhao4,Xu Dezhu1,Guo Tenglong1,Huang Genping3,Kühn Fritz E.5,Zhang Bo12ORCID,Zhang Tao1

Affiliation:

1. CAS Key Laboratory of Science and Technology on Applied Catalysis Dalian Institute of Chemical Physics, Chinese Academy of Sciences Dalian 116023 China

2. University of Chinese Academy of Sciences Beijing 100049 China

3. Department of Chemistry, School of Science and Tianjin Key Laboratory of Molecular Optoelectronic Sciences Tianjin University Tianjin 300072 China

4. School of Chemistry and Chemical Engineering Inner Mongolia University 235 West University Street Hohhot 010021 China

5. Molecular Catalysis, Catalysis Research Center and Department of Chemistry, School of Natural Sciences Technical University of Munich Lichtenbergstr. 4 D – 85748 Garching bei München

Abstract

AbstractAn efficiently catalyzed synthesis of pharmaceutically relevant 1,2,3‐trazoles from renewable resources is highly desirable. However, due to incompatible catalysis conditions, this endeavor remained challenging so far. Herein, a practical access protocol to 1,2,3‐triazoles, starting from lignin phenolic β‐O‐4 with γ‐OH group utilizing a vanadium‐based catalyst is presented. A broad substrate scope reaching up to 97 % yield of 1,2,3‐triazoles are obtained. The reaction pathway includes selective cleavage of double C−O bonds, cycloaddition, and dehydrogenation. Mechanistic studies and density‐functional theory (DFT) calculations suggest that the V‐based complex acts as a bifunctional catalyst for both selective C−O bonds cleavage and dehydrogenation. This synthetic pathway has been applied for the synthesis of pharmacological and biological active carbohydrate derivatives starting from biomass components as feedstock, enabling a potential sustainable route to triazolyl carbohydrate derivatives, which paves the way for lignin‐based heterocyclic aromatics in the pharmaceutical applications.

Funder

National Natural Science Foundation of China

Technische Universität München

Publisher

Wiley

Subject

General Energy,General Materials Science,General Chemical Engineering,Environmental Chemistry

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