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Synthesis 2022; 54(09): 2081-2102
DOI: 10.1055/a-1701-7397
DOI: 10.1055/a-1701-7397
review
Recent Advances in Palladium-Catalyzed Oxidative Couplings in the Synthesis/Functionalization of Cyclic Scaffolds Using Molecular Oxygen as the Sole Oxidant
We are grateful for financial support in the form of funding and fellowships provided by the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) (São Paulo Research Foundation) (Grant Nos. 2014/50249-8, 2020/10246-0, 2020/01255-6), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) (Coordination for the Improvement of Higher Education Personnel) (Finance Code 001), the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) (The Brazilian National Council for Scientific and Technological Development) and GlaxoSmithKline (GSK).
Abstract
Over the past years, Pd(II)-catalyzed oxidative couplings have enabled the construction of molecular scaffolds with high structural diversity via C–C, C–N and C–O bond-forming 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 for 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 of 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
Key words
palladium - oxidative coupling - oxidative functionalization - oxygen - oxidative cyclizationPublication History
Received: 15 September 2021
Accepted after revision: 19 November 2021
Accepted Manuscript online:
19 November 2021
Article published online:
25 January 2022
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart
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