Novel lignin-supported copper complex as a highly efficient and recyclable nanocatalyst for Ullmann reaction

Baichuan Mo; Zhanyu Li; Jinsong Peng; Chunxia Chen

doi:10.1016/j.ijbiomac.2023.124263

Novel lignin-supported copper complex as a highly efficient and recyclable nanocatalyst for Ullmann reaction

Int J Biol Macromol. 2023 Jun 1:239:124263. doi: 10.1016/j.ijbiomac.2023.124263. Epub 2023 Mar 31.

Authors

Baichuan Mo¹, Zhanyu Li², Jinsong Peng³, Chunxia Chen⁴

Affiliations

¹ College of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, Harbin, Heilongjiang 150040, China; Material Science and Engineering College, Northeast Forestry University, Harbin, Heilongjiang 150040, China.
² College of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, Harbin, Heilongjiang 150040, China.
³ College of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, Harbin, Heilongjiang 150040, China. Electronic address: jspeng1998@163.com.
⁴ College of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, Harbin, Heilongjiang 150040, China; Material Science and Engineering College, Northeast Forestry University, Harbin, Heilongjiang 150040, China. Electronic address: ccx1759@163.com.

PMID: 37004929
DOI: 10.1016/j.ijbiomac.2023.124263

Abstract

In this work, we prepared polyhydroxylated lignin by demethylation and hydroxylation of lignin, and grafted phosphorus-containing groups by nucleophilic substitution reaction, the resulting material could be used as a carrier for the preparation of heterogeneous Cu-based catalysts (PHL-CuI-OPR₂). The optimal PHL-CuI-OP^tBu₂ catalyst was characterized by FT-IR, TGA, BET, XRD, SEM-EDS, ICP-OES, XPS. The catalytic performance of PHL-CuI-OP^tBu₂ in the Ullmann CN coupling reaction was evaluated using iodobenzene and nitroindole as model substrates under nitrogen atmosphere with DME and H₂O as cosolvent at 95 °C for 24 h. The applicability of modified lignin-supported copper catalyst was investigated of various aryl/heteroaryl halides with indoles under optimal conditions, the corresponding products were obtained with high yield. Additionally, it could be easily recovered from the reaction medium by an easy centrifugation and washing.

Keywords: Copper complex; Heterogeneous nanocatalyst; Lignin; Ullmann reaction.

MeSH terms

Catalysis
Copper* / chemistry
Lignin*
Spectroscopy, Fourier Transform Infrared

Substances

Copper
Lignin