Application of Raw and Chemically Modified Biomasses for Heterogeneous Cu-Catalysed Conversion of Aryl boronic Acids to Phenols Derivatives

Author:

Torres Fernanda GuimarãesORCID,Teodoro Filipe Simões,Gurgel Leandro Vinícius AlvesORCID,Bourdreux Flavien,Zayene Olfa,Gaucher AnneORCID,Gil Laurent FrédéricORCID,Prim DamienORCID

Abstract

This work describes the application of raw and chemically modified cellulose and sugarcane bagasse for ipso-hydroxylation of aryl boronic acids in environmentally friendly reaction conditions. The catalytic efficiency of five support-[Cu] materials was compared in forming phenols from aryl boronic acids. Our investigation highlights that the CEDA-[Cu] material (6-deoxy-6-aminoethyleneamino cellulose loaded with Cu) leads to the best results under very mild reaction conditions. The optimized catalytic sequence, allowing a facile transformation of boronic acids to phenols, required the mandatory and joint presence of the support, Cu2O, and KOH at room temperature. CEDA-[Cu] was characterized using 13C solid-state NMR, ICP, and FTIR. The use of CEDA-[Cu] accounts for the efficacious synthesis of variously substituted phenol derivatives and presents very good recyclability after five catalytic cycles.

Funder

Universidade Federal de Ouro Preto

Fundação de Amparo à Pesquisa do Estado de Minas Gerais

National Council for Scientific and Technological Development

Agence Nationale de la Recherche

French National Centre for Scientific Research

University of Paris-Saclay

Versailles Saint-Quentin-en-Yvelines University

French Ministère de l’Enseignement Supérieur et de la Recherche

Publisher

MDPI AG

Subject

Physical and Theoretical Chemistry,Catalysis

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