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

Fernanda Guimarães Torres (1, 2, 3) , Filipe Simões Teodoro (2) , Leandro Vinícius Alves Gurgel (2) , Flavien Bourdreux (1, 3) , Olfa Zayene (1, 3) , Anne Gaucher (1, 3) , Laurent Frédéric Gil (2) , Damien Prim (1, 3)

1 ILV - Institut Lavoisier de Versailles
2 UFOP - Universidade Federal de Ouro Preto
3 Université Paris-Saclay

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-6aminoethyleneamino 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 using13C 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.

Mots clés: Cellulose; Copper; Heterogeneous catalysis; Ipso-hydroxylation; Phenol

Domaines: Catalyse

Fernanda Guimarães Torres, Filipe Simões Teodoro, Leandro Vinícius Alves Gurgel, Flavien Bourdreux, Olfa Zayene, et al.. Application of Raw and Chemically Modified Biomasses for Heterogeneous Cu-Catalysed Conversion of Aryl boronic Acids to Phenols Derivatives. Catalysts, 2022, 12 (1), ⟨10.3390/catal12010092⟩. ⟨hal-03554174⟩