Three‐Component Povarov Reaction with Alcohols as Alkene Precursors: Efficient Access to 2‐Arylquinolines. Issue 3 (23rd January 2017)

• Record Type: Journal Article
• Authors: Li, Xinjian; Xing, Qi; Li, Pan; Zhao, Jingjing; Li, Fuwei
• Is Part Of: European journal of organic chemistry. Issue 3(2017)
• Page Start: 618
• Page End: 625
• Publication Date: 2017-01-23
• Subjects: Quinolines -- Nitrogen heterocycles -- Iron -- Homogeneous catalysis -- Alcohols -- Cascade reactions; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601343
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An atom‐economic and efficient approach to the synthesis of 2‐arylquinolines has been developed. The protocol involves an iron‐catalysed cascade N ‐alkylation/aerobic oxidation/Povarov reaction, and the desired quinolines were prepared in moderate to excellent yields from readily accessible anilines, aldehydes, and EtOH/ n PrOH, with water as the only side‐product. The aniline substrates also act as a recyclable transfer medium for EtOH/ n PrOH through an in‐situ N ‐alkylation/oxidation process. This makes EtOH/ n PrOH an economical and environmentally friendly precursor of alkenes as well as the solvent. Abstract : An atom‐economic and facile approach to the synthesis of 2‐arylquinolines has been developed. The protocol involves an iron‐catalysed cascade N ‐alkylation/aerobic oxidation/Povarov reaction, and the desired quinolines were prepared in moderate to excellent yields from readily accessible anilines, aldehydes, and EtOH/ n PrOH, with water as the only side‐product.