Lignin Tandem Catalytic Transformation to Phenolic Aryl Acrylic Esters as Plant Growth Regulators.

Abstract

Based on the concept "Derived from Agroforestry, belong to (Servicing) Agroforestry", we herein achieved the tandem catalytic transformation of lignin to phenolic aryl acrylic esters, which can work as plant growth regulators. The transformation involves the first catalytic oxidative fractionation (COF) of lignin into aromatic aldehydes, which can further undergo Knoevenagel condensation with acids/esters with active C_α-H to generate the phenolic aryl acrylic esters. For the first lignin transformation, the Cu salt (CuSO₄) in a 7.5 wt % NaOH aqueous solution could achieve the selective cleavage of lignin C-C bonds to provide a 25.0 wt % yield of aromatic aldehydes. Subsequently, the unique basic sites of the self-assembled hybrid system of CeO₂ and 2-cyanopyridine could overcome the limitations of traditional homogeneous/heterogeneous bases and facilitate the condensation between phenolic-containing aromatic aldehydes and malonic ester to aryl acrylic esters. Furthermore, the lignin-based phenolic aryl acrylic esters showed different plant growth regulation activity based on the various structural groups for peppermint seed cultivation. The above results can expand the high-value utilization of lignin in the agroforestry field.