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Iron-Catalyzed Meerwein Carbooxygenation of Electron-Rich Olefins: Studies with Styrenes, Vinyl Pyrrolidinone, and Vinyl Oxazolidinone.
de Souza, Edson Leonardo Scarpa; Wiethan, Carson; Correia, Carlos Roque Duarte.
Afiliação
  • de Souza ELS; Department of Organic Chemistry, Institute of Chemistry, University of Campinas, Rua Josué de Castro, 13083-970 Campinas, São Paulo, Brazil.
  • Wiethan C; Department of Organic Chemistry, Institute of Chemistry, University of Campinas, Rua Josué de Castro, 13083-970 Campinas, São Paulo, Brazil.
  • Correia CRD; Department of Organic Chemistry, Institute of Chemistry, University of Campinas, Rua Josué de Castro, 13083-970 Campinas, São Paulo, Brazil.
ACS Omega ; 4(20): 18918-18929, 2019 Nov 12.
Article em En | MEDLINE | ID: mdl-31737853
The arylative oxygenation of the electron-rich olefins styrene, α-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.

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: ACS Omega Ano de publicação: 2019 Tipo de documento: Article País de afiliação: Brasil País de publicação: Estados Unidos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: ACS Omega Ano de publicação: 2019 Tipo de documento: Article País de afiliação: Brasil País de publicação: Estados Unidos