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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Iron-Catalyzed Meerwein Carbooxygenation of Electron-Rich Olefins: Studies with Styrenes, Vinyl Pyrrolidinone, and Vinyl Oxazolidinone

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Author(s):
Scarpa de Souza, Edson Leonardo [1] ; Wiethan, Carson [1] ; Duarte Correia, Carlos Roque [1]
Total Authors: 3
Affiliation:
[1] Univ Estadual Campinas, Inst Chem, Dept Organ Chem, Rua Josue de Castro, BR-13083970 Campinas, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: ACS OMEGA; v. 4, n. 20, p. 18918-18929, NOV 12 2019.
Web of Science Citations: 0
Abstract

The arylative oxygenation of the electron-rich olefins styrene, a-methylstyrene, vinyl pyrrolidinone, and vinyl oxazolidinone was accomplished using arenediazonium salts and catalytic amounts of FeSO4 in an effective single electron transfer radical process. A broad range of aryldiazonium salts was tolerated using water, methanol, or their combination with acetonitrile to furnish the corresponding carbohydroxylated and carbomethoxylated products (42 examples), including functionalized dihydroisocoumarin and dihydrobenzofuran systems in good to excellent yields (up to 88%). The protocols developed for the Fe(II)catalyzed carbohydroxylation were also compared to Ru(II) and Ir(III) photoredox carbooxygenations of these electron-rich olefins. The Fe(II)catalyzed process proved to be highly competitive compared to the photoredox and the uncatalyzed processes. The proposed mechanism for the Fe(II)-catalyzed reactions involves the synergic combination with an effective Fe+2/Fe+3 redox system and a radical polar crossover mechanism featuring an unprecedented capture of the reactive N-acyliminium in the case of vinyl pyrrolidinone and vinyl oxazolidinone. (AU)

FAPESP's process: 18/08627-6 - Nickel catalyzed stereoselective C-C coupling reactions: design, evaluation of ligands, and synthetic applications
Grantee:Carson Wanderley Wiethan
Support Opportunities: Scholarships in Brazil - Post-Doctoral
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
Grantee:Carlos Roque Duarte Correia
Support Opportunities: Research Projects - Thematic Grants