Jump to main content
Jump to site search

Issue 24, 2016
Previous Article Next Article

Palladium-catalyzed β-C(sp3)–H arylation of phthaloyl alanine with hindered aryl iodides: synthesis of complex β-aryl α-amino acids

Author affiliations

Abstract

An efficient protocol for palladium-catalyzed β-C(sp3)–H arylation of aliphatic carboxamides equipped with a 2-(2-pyridyl) ethylamine (PE) auxiliary was developed. The PE auxiliary is uniquely effective at facilitating the arylation of primary C(sp3)–H bonds with sterically hindered aryl iodides. A variety of aryl iodides bearing alkoxyl, carbonyl, nitro and halogen groups on the ortho position can react with the PE-coupled phthaloyl alanine substrate in moderate to excellent yield. These reactions offer a useful solution for preparing complex β-aryl α-amino acid products from readily accessible starting materials.

Graphical abstract: Palladium-catalyzed β-C(sp3)–H arylation of phthaloyl alanine with hindered aryl iodides: synthesis of complex β-aryl α-amino acids

  • This article is part of the themed collection: New Talent
Back to tab navigation

Supplementary files

Publication details

The article was received on 16 Dec 2015, accepted on 12 Jan 2016 and first published on 12 Jan 2016


Article type: Communication
DOI: 10.1039/C5OB02580J
Citation: Org. Biomol. Chem., 2016,14, 5511-5515
  •   Request permissions

    Palladium-catalyzed β-C(sp3)–H arylation of phthaloyl alanine with hindered aryl iodides: synthesis of complex β-aryl α-amino acids

    X. Zhang, G. He and G. Chen, Org. Biomol. Chem., 2016, 14, 5511
    DOI: 10.1039/C5OB02580J

Search articles by author

Spotlight

Advertisements