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Photoinduced Five-Component Radical Relay Aminocarbonylation of Alkenes.
Lu, Bin; Zhang, Zhihan; Jiang, Min; Liang, Dong; He, Zi-Wei; Bao, Feng-Shuo; Xiao, Wen-Jing; Chen, Jia-Rong.
Afiliación
  • Lu B; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, China.
  • Zhang Z; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, China.
  • Jiang M; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, China.
  • Liang D; College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 310036, China.
  • He ZW; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, China.
  • Bao FS; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, China.
  • Xiao WJ; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, China.
  • Chen JR; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, China.
Angew Chem Int Ed Engl ; 62(41): e202309460, 2023 Oct 09.
Article en En | MEDLINE | ID: mdl-37615886
Radical single carbonylation reactions with CO constitute a direct and robust strategy toward various carbonyl compounds from readily available chemicals, and have been extensively studied over the past decades. However, realizing highly selective catalytic systems for controlled radical double carbonylation reactions has remained a substantial challenge, particularly for the more advanced multicomponent variants, despite their great potential value. Herein, we report a visible-light-driven radical relay five-component radical double aminocarbonylation reaction of unactivated alkenes using CO under metal-free conditions. This protocol provides direct access to valuable γ-trifluoromethyl α-ketoamides with good yields and high chemoselectivity. Crucial was the identification of distinct dual roles of amine coupling partners, sequentially acting as electron donors for the formation of photoactive electron donor-acceptor (EDA) complexes with radical precursors and then as a CO acceptor via nitrogen radical cations to form carbamoyl radicals. Cross-coupling of carbamoyl radicals with the acyl radicals that are formed in an alkene-based relay process affords double aminocarbonylation products.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2023 Tipo del documento: Article País de afiliación: China Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2023 Tipo del documento: Article País de afiliación: China Pais de publicación: Alemania