title: Copper-catalyzed synthesis of medium- and large-sized nitrogen heterocycles via N-arylation of phosphoramidates and carbamates.
abstract: [reaction: see text] We have developed an efficient method for the preparation of medium- and large-sized nitrogen heterocycles via copper-catalyzed intramolecular N-arylation of phosphoramidates and carbamates. Introduction of the phosphoryl group or tert-butoxycarbonyl at N-termini can improve intramolecular cyclization under copper catalysis, and the phosphoryl and tert-butoxycarbonyl can easily be removed under the mild conditions; thus, the convenient and efficient method is suitable for the preparation of medium- and large-sized nitrogen heterocycles.
authors.affiliation: Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, PR China.
authors.forename: Ting
authors.initials: T
authors.lastname: Yang
authors.forename: Changxue
authors.initials: C
authors.lastname: Lin
authors.forename: Hua
authors.initials: H
authors.lastname: Fu
authors.forename: Yuyang
authors.initials: Y
authors.lastname: Jiang
authors.forename: Yufen
authors.initials: Y
authors.lastname: Zhao
mesh_terms: D000577:Amides / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry*
chemical_list: D000577:Amides; D001555:Benzene Derivatives; D002219:Carbamates; D006574:Heterocyclic Compounds, 2-Ring; D010756:Phosphoric Acids; D003300:Copper; C011067:phosphoramidic acid; D009584:Nitrogen