Preparation of supported palladium catalysts for the Heck-Matsuda reaction enantioselective in continuous flow

• Grant number: 15/07773-0
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: September 01, 2015
• End date: August 31, 2017
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Carlos Roque Duarte Correia
• Grantee: Rafael de Lima Oliveira
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

The Heck reaction is one of most versatile tool in organic chemistry and it has been used in many areas such as synthesis of natural products and functional materials. The reaction is usually running with a homogeneous palladium catalyst, thus, the catalyst recovering is a difficult task which can result to contamination of the desired products with metal. From the point of view of green chemistry, the development of more environmental friendly conditions is very desirable, for example, the use of heterogeneous palladium catalyst. Many heterogeneous catalysts were already developed, but resulting often in materials with lower activity when compared to the homogeneous counterpart. Moreover, the activity of recycled catalysts gradually decreases due to metal leaching, particle growth and composition change. To solve these problems, new methodologies to produce heterogeneous catalysts very active are necessary, especially for enantioselective processes.The goal of this project is to develop active palladium catalysts to promote the enantioselective Heck-Matsuda reaction. For this, homogeneous palladium catalysts will be immobilized in different supports such as MCM-41, carbon nanotubes, Merrifield and Wang resins and to test their catalytic properties activity, selectivity and stability to convert olefins. The reactions will be run in batch and microreactors of continuous flux. The use of continuous flux for cross coupling reaction is not new, however, the majority of these studies were done using homogeneous catalysts, thus, this process using heterogeneous catalysts generates a new scientific challenge.

Scientific publications

(4)

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

OLIVEIRA, RAFAEL L.; NIJHOLT, TOM; SHAKERI, MOZAFFAR; DE JONGH, PETRA E.; GEBBINK, ROBERTUS J. M. KLEIN; DE JONG, KRIJN P.. Encapsulation of chiral Fe(salen) in mesoporous silica structures for use as catalysts to produce optically active sulfoxides. CATALYSIS SCIENCE & TECHNOLOGY, v. 6, n. 13, p. 5124-5133, 2016. (15/07773-0)

PREDIGER, PATRICIA; CHEMINSKI, THAIS; NEVES, TAUANY DE FIGUEIREDO; NUNES, WILLIAM BARDELIN; SABINO, LIVIA; FRANCO PICONE, CAROLINA SIQUEIRA; OLIVEIRA, RAFAEL L.; DUARTE CORREIA, CARLOS ROQUE. Graphene oxide nanomaterials for the removal of non-ionic surfactant from water. JOURNAL OF ENVIRONMENTAL CHEMICAL ENGINEERING, v. 6, n. 1, p. 1536-1545, FEB 2018. (15/07033-7, 15/07773-0)

OLIVEIRA, RAFAEL L.; OLIVEIRA, CRISTINE S.; LANDERS, RICHARD; CORREIA, CARLOS R. D.. Pd Nanoparticles Immobilized on Graphene Oxide/Silica Nanocomposite: Efficient and Recyclable Catalysts for Cross-Coupling Reactions. CHEMISTRYSELECT, v. 3, n. 2, p. 535-543, JAN 17 2018. (14/25770-6, 15/07773-0)

OLIVEIRA, RAFAEL L.; KERSTIEN, JULIUS; SCHOMAECKER, REINHARD; THOMAS, ARNE. Pd nanoparticles confined in mesoporous N-doped carbon silica supports: a synergistic effect between catalyst and support. CATALYSIS SCIENCE & TECHNOLOGY, v. 10, n. 5, p. 1385-1394, MAR 7 2020. (15/07773-0)