Recent Developments on Palladium-Catalyzed Carbonylation Reactions in Renewable Solvents

Palladium-catalyzed carbonylation reaction has surfaced as a robust tool for insertion of the carbonyl group into organic molecules, and in the last decades enormous progress has been made. Nowadays, a plethora of methodologies is available to synthesize all kinds of carbonyl compounds. However, the focus has shifted during recent years to address rising concerns related to developing safe, cost-efficient, and more sustainable methodologies. The use of different carbon monoxide (CO) precursors/sources, avoiding handling of highly toxic and flammable gaseous carbon monoxide, and substituting nonrenewable solvents for those derived from renewable feedstock have contributed to aim these goals. In this review, we will discuss the advent of the application of renewable solvents to improve the sustainability and environmentally benign nature of Pd catalyzed carbonylation reactions.

Keywords:
palladium-catalyzed; carbon monoxide; carbonylation reactions; renewable solvent; sustainability

Authorship

Danilo Y. de Albuquerque

Laboratório de Síntese, Catálise e Modelagem Molecular (SintCatMol), Centro de Excelência para Pesquisa em Química Sustentável (CERSusChem), Departamento de Química, Universidade Federal de São Carlos (UFSCar), Rodovia Washington Luís, km 235, SP-310, 13565-905 São Carlos-SP, BrazilUniversidade Federal de São Carlos (UFSCar)BrazilSão Carlos, SP, BrazilLaboratório de Síntese, Catálise e Modelagem Molecular (SintCatMol), Centro de Excelência para Pesquisa em Química Sustentável (CERSusChem), Departamento de Química, Universidade Federal de São Carlos (UFSCar), Rodovia Washington Luís, km 235, SP-310, 13565-905 São Carlos-SP, Brazil

Danilo Y. de Albuquerque was born in Batayporã, MS, Brazil, in 1991. He studied Chemistry at the Federal University of Grande Dourados (Brazil) and obtained Master’s degree in 2017, from the same University. Since 2017 he joined the research group of Prof Dr Ricardo S. Schwab at the Federal University of São Carlos (Brazil), where he is currently conducting his PhD studies. His research focuses on the development of new palladium-catalyzed carbonylation reactions, and more particularly on the following subjects: functionalization of triazoles and synthesis of aryl selenoesters through carbonylation reactions.

Wystan K. O. Teixeira

Wystan K. O. Teixeira was born in Catanduva, SP, Brazil, in 1990. He studied Chemistry at the Federal University of Rio Grande (Brazil) and obtained Master’s degree in 2017, from the same University. Since 2018 he has been a PhD student in Chemistry at the Federal University of São Carlos (UFSCar), under the guidance of Prof Dr Ricardo S. Schwab, working in the field of Organic Chemistry. His project is based on the synthesis of selenoheterocycles fused with 1,2,3-triazoles compounds and their application in Medicinal Chemistry.

Senthil Narayanaperumal

Libbs Farmacêutica Ltda., Av. Dona Cesária Camargo de Oliveira, 633, Jardim Vista Alegre, 06807-320 Embu das Artes-SP, BrazilLibbs Farmacêutica Ltda.BrazilEmbu das Artes, SP, BrazilLibbs Farmacêutica Ltda., Av. Dona Cesária Camargo de Oliveira, 633, Jardim Vista Alegre, 06807-320 Embu das Artes-SP, Brazil

Senthil Narayanaperumal was born in Nagercoil (India) in 1981. He graduated from M.S. University, Tirunelveli, India, and received his MSc in Applied Chemistry in 2005 from the National Institute of Technology (NIT), India. He obtained his PhD in 2010 from the Federal University of Santa Maria (UFSM), Brazil. He immediately began postdoctoral studies at the Federal University of São Carlos (UFSCar), and then Federal University of Rio Grande do Sul (UFRGS), Brazil. In 2015, he began industrial research activity at Cristália Pharmaceutical Ltd, Itapira, Brazil. Presently, he is associated with the Libbs Pharmaceutical Ltd, São Paulo, Brazil. His research interests are focused on ionic-liquid mediated organic transformations, asymmetric organocatalysis, and synthesis of active pharmaceutical intermediates.

Ricardo S. Schwab ^**e-mail: rschwab@ufscar.br

Ricardo S. Schwab received his Bachelor’s degree in Industrial Chemistry in 2005 at the University of Santa Cruz do Sul and PhD degree in Organic Chemistry in 2010, under the supervision of Prof Dr Antonio L. Braga at the Federal University of Santa Maria and co-supervision of Prof Dr Ludger Wessjohann from Leibniz Institute of Plant Biochemistry, Halle Salle, Germany. In 2011 he spent two years in postdoctoral research at the Federal University of Rio Grande do Sul. Two years later, Ricardo established his independent research group in the Department of Chemistry at Federal University of São Carlos (UFSCar) and recently became Associate Professor. His research focuses mainly on the development of more sustainable catalytic methodologies and on transition metal catalysis involving carbon monoxide.

https://orcid.org/0000-0001-8722-9403

*e-mail: rschwab@ufscar.br

Editor handled this article: Teodoro S. Kaufman

Danilo Y. de Albuquerque was born in Batayporã, MS, Brazil, in 1991. He studied Chemistry at the Federal University of Grande Dourados (Brazil) and obtained Master’s degree in 2017, from the same University. Since 2017 he joined the research group of Prof Dr Ricardo S. Schwab at the Federal University of São Carlos (Brazil), where he is currently conducting his PhD studies. His research focuses on the development of new palladium-catalyzed carbonylation reactions, and more particularly on the following subjects: functionalization of triazoles and synthesis of aryl selenoesters through carbonylation reactions.

Wystan K. O. Teixeira was born in Catanduva, SP, Brazil, in 1990. He studied Chemistry at the Federal University of Rio Grande (Brazil) and obtained Master’s degree in 2017, from the same University. Since 2018 he has been a PhD student in Chemistry at the Federal University of São Carlos (UFSCar), under the guidance of Prof Dr Ricardo S. Schwab, working in the field of Organic Chemistry. His project is based on the synthesis of selenoheterocycles fused with 1,2,3-triazoles compounds and their application in Medicinal Chemistry.

Senthil Narayanaperumal was born in Nagercoil (India) in 1981. He graduated from M.S. University, Tirunelveli, India, and received his MSc in Applied Chemistry in 2005 from the National Institute of Technology (NIT), India. He obtained his PhD in 2010 from the Federal University of Santa Maria (UFSM), Brazil. He immediately began postdoctoral studies at the Federal University of São Carlos (UFSCar), and then Federal University of Rio Grande do Sul (UFRGS), Brazil. In 2015, he began industrial research activity at Cristália Pharmaceutical Ltd, Itapira, Brazil. Presently, he is associated with the Libbs Pharmaceutical Ltd, São Paulo, Brazil. His research interests are focused on ionic-liquid mediated organic transformations, asymmetric organocatalysis, and synthesis of active pharmaceutical intermediates.

Ricardo S. Schwab received his Bachelor’s degree in Industrial Chemistry in 2005 at the University of Santa Cruz do Sul and PhD degree in Organic Chemistry in 2010, under the supervision of Prof Dr Antonio L. Braga at the Federal University of Santa Maria and co-supervision of Prof Dr Ludger Wessjohann from Leibniz Institute of Plant Biochemistry, Halle Salle, Germany. In 2011 he spent two years in postdoctoral research at the Federal University of Rio Grande do Sul. Two years later, Ricardo established his independent research group in the Department of Chemistry at Federal University of São Carlos (UFSCar) and recently became Associate Professor. His research focuses mainly on the development of more sustainable catalytic methodologies and on transition metal catalysis involving carbon monoxide.

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