Gold-amine cooperative catalysis for reductions and reductive aminations using formic acid as hydrogen source

Author(s)

Fiorio, Jhonatan L. ^{[1, 2]} ; Araujo, Thaylan P. ^[1] ; Barbosa, Eduardo C. M. ^[1] ; Quiroz, Jhon ^[1] ; Camargo, Pedro H. C. ^[1] ; Rudolph, Matthias ^[2] ; Hashmi, A. Stephen K. ^[2] ; Rossi, Liane M. ^[1]

Affiliation

^[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Av Prof Linen Prestes 748, BR-05508000 Sao Paulo, SP - Brazil

^[2] Heidelberg Univ, Organisch Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg - Germany

• Document type: Journal article
• Source: APPLIED CATALYSIS B-ENVIRONMENTAL; v. 267, JUN 15 2020.
• Web of Science Citations: 0

Abstract

Selective hydrogenation of alkynes to alkenes and reductive amination are industrially important reactions to synthesize a variety of fine and bulk chemicals. We report herein on a green and convenient approach for Z-alkenes and secondary amines using gold catalyst and formic acid (FA) as a green reductant. Furthermore, we highlight that the key to successfully obtain high reaction rates is to use an appropriate amine, which acts cooperatively with the gold surface, to activate formic acid. Studies with deuterium-labeled hydrogen donors gave insights that the decomposition of Au-formate species is involved in the rate-determining step. Moreover, various valuable secondary amines could be synthetized from readily available nitro and carbonyl compounds. This new strategy provides a cleaner, safer, more efficient and selective way to catalyze the synthesis of Z-alkenes and valuable amines. (AU)

• FAPESP's process: 15/11452-5 - Hybrid materials composed of oxides and metallic nanoparticles for catalytic and photocatalytic applications
• Grantee: Eduardo César Melo Barbosa
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• FAPESP's process: 15/21366-9 - HYBRID MATERIALS CONTAINING METAL NANOPARTICLES FOR CATALYTIC APPLICATIONS
• Grantee: Pedro Henrique Cury Camargo
• Support Opportunities: Regular Research Grants
• FAPESP's process: 15/26308-7 - Optimization of the physicochemical properties of nano -structured materials for applications in molecular recognition, catalysis and energy conversion/storage
• Grantee: Roberto Manuel Torresi
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 16/17866-9 - Tailoring the catalytic properties of plasmonic Nanorattles towards the photochemical activation of oxygen under mild conditions
• Grantee: Jhon Jhon Quiroz Torres
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 17/07564-8 - Hybrid nanomaterials for energy conversion: integrating plasmonic nanostructures and photoluminescent nanomaterials
• Grantee: Thaylan Pinheiro Araújo
• Support Opportunities: Scholarships in Brazil - Master
• FAPESP's process: 16/16738-7 - Study of the influence of organic ligands on the reactivity of gold nanoparticles
• Grantee: Liane Marcia Rossi
• Support Opportunities: Regular Research Grants