Synthesis
DOI: 10.1055/a-1701-7397
review

Recent advances in Pd-catalyzed oxidative couplings in the synthesis/functionalization of cyclic scaffolds using molecular oxygen as the sole oxidant

Amanda Aline Barboza
1  Chemistry, Federal University of São Carlos, São Carlos, Brazil
,
Juliana Arantes Dantas
1  Chemistry, Federal University of São Carlos, São Carlos, Brazil
,
Mateus Oliveira Costa
1  Chemistry, Federal University of São Carlos, São Carlos, Brazil
,
Attilio Chiavegatti
1  Chemistry, Federal University of São Carlos, São Carlos, Brazil
,
Guilherme Augusto de Melo Jardim
1  Chemistry, Federal University of São Carlos, São Carlos, Brazil
,
2  Chemistry, Federal University of São Carlos, São Carlos, Brazil
› Author Affiliations
Supported by: Fundação de Amparo à Pesquisa do Estado de São Paulo 2014/50249-8,2020/01255-6,2020/10246-0
Supported by: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior Finance Code 001
Supported by: GlaxoSmithKline
Supported by: Conselho Nacional de Desenvolvimento Científico e Tecnológico

Over the past years, Pd(II)-catalyzed oxidative couplings enabled the achievement of molecular scaffolds with high structural diversity via C−C, C-N and C-O bond-formation reactions. In contrast to the use of stoichiometric amounts of more common oxidants, such as metal salts (Cu and Ag) and benzoquinone derivatives, the use of molecular oxygen in the direct or indirect regeneration of Pd(II) species presents itself as a more viable alternative in terms of economy and sustainability. In this review, we describe recent advances on the development Pd-catalyzed oxidative cyclizations/functionalizations, where molecular oxygen plays a pivotal role as the sole stoichiometric oxidant. 1 Introduction 2 Oxidative C-C and C-Nu Coupling 2.1 Intramolecular Oxidative C-Nu Heterocyclization Reactions 2.1.1 C-H Activation 2.1.2 Wacker/aza-Wacker Type Cyclization 2.1.3 Tandem Wacker/aza-Wacker and Cyclization/Cross Coupling Reactions 2.2 Intermolecular Oxidative C-Nu Heterocoupling Reactions 2.3 Intramolecular Oxidative (C-C) Carbocyclization Reactions 2.4 Intermolecular Oxidative C-C Coupling Reactions 2.4.1 Cyclization Reactions 2.4.2 Cross-Coupling Reactions 2.4.3 Homo-Coupling Reactions 3 Aerobic Dehydrogenative Coupling/Functionalization 4 Oxidative C-H Functionalization 5 Summary



Publication History

Received: 15 September 2021

Accepted after revision: 19 November 2021

Publication Date:
19 November 2021 (online)

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