An efficient method was developed for the one-pot construction of pyrrolo[1,2-]quinoxalines a Cu(II)-catalyzed domino reaction between 2-(1-pyrrol-1-yl)anilines and alkylsilyl peroxides. This reaction proceeds through C-C bond cleavage and new C-C and C-N bond formation. A mechanistic study suggests that alkyl radical species participate in the cascade reaction.
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http://dx.doi.org/10.1039/d3ob01934a | DOI Listing |
Chem Sci
March 2024
School of Chemical Engineering and Light Industry, Guangdong University of Technology Guangzhou 510006 China
α-Keto-, β-acetoxy- and β-amidoalkylsilyl peroxides are prepared from various precursors and utilized for Fe-catalyzed and visible-light-promoted radical functionalization with coupling partners under mild conditions with a broad substrate scope.
View Article and Find Full Text PDFOrg Biomol Chem
March 2024
College of Pharmacy, Key Laboratory of Protection, Development and Utilization of Medicinal Resources in Liupanshan Area, Ministry of Education, Ningxia Medical University, Yinchuan, Ningxia Hui Autonomous Region, China.
An efficient method was developed for the one-pot construction of pyrrolo[1,2-]quinoxalines a Cu(II)-catalyzed domino reaction between 2-(1-pyrrol-1-yl)anilines and alkylsilyl peroxides. This reaction proceeds through C-C bond cleavage and new C-C and C-N bond formation. A mechanistic study suggests that alkyl radical species participate in the cascade reaction.
View Article and Find Full Text PDFJ Org Chem
February 2023
Laboratory of Organocatalytic Chemistry, Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo, Kyoto 606-8501, Japan.
The hitherto difficult site-selective -methoxybenzylation of secondary amides using -methoxybenzylated alkylsilyl peroxides as a novel -methoxybenzylation agent under copper catalysis is reported. The reaction proceeds under mild reaction conditions in a highly chemoselective manner. This approach was successfully applied to the site-selective -methoxybenzylation of peptides.
View Article and Find Full Text PDFJ Org Chem
July 2022
School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China.
An Fe(OTf)-catalyzed three-component coupling reaction of α,β,γ,δ-unsaturated carbonyl compounds with alkylsilyl peroxides in the presence of certain heteronucleophiles (ROH and indole) is realized under mild reaction conditions. A variety of α,β,γ,δ-diene carbonyl substrates with different substituents were successfully employable via combination with several different alkylsilyl peroxides. This new approach is also applicable to the double functionalization of diene substrates.
View Article and Find Full Text PDFOrg Lett
April 2022
School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China.
The formation of two carbon-carbon bonds using vinylarenes with alkylsilyl peroxides and β-keto carbonyl substrates is effected by the presence of catalytic Fe(OTf) under mild reaction conditions. A variety of vinylarenes with different substituents can be utilized in combination with several different alkylsilyl peroxides and β-keto carbonyl substrates.
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