Synthesis of Medium Ring Nitrogen Heterocycles via a Tandem Copper-Catalyzed C-N Bond Formation-Ring-Expansion Process

Journal of the American Chemical Society

Volumn 126, Issue 11, 2004, Pages 3529-3533

  Klapars, Artis ^a   Parris, Sean ^a   Anderson, Kevin W ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; CATALYSIS; COMPLEXATION; SYNTHESIS (CHEMICAL);

BOND FORMATION; TANDEMS;

NITROGEN COMPOUNDS;

ACETIC ACID; BETA LACTAM DERIVATIVE; BROMINE DERIVATIVE; CARBON; COPPER DERIVATIVE; HETEROCYCLIC COMPOUND; IODIDE; METAL COMPLEX; NITROGEN DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; METAL BINDING; PROCESS DESIGN; PROCESS MODEL; RING EXPANSION PROCESS; SYNTHESIS;

AMINES; BENZENE DERIVATIVES; CATALYSIS; COPPER; CYCLIZATION; HETEROCYCLIC COMPOUNDS, 2-RING; LACTAMS;

EID: 1642298324     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038565t     Document Type: Article

References (21)

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19. It is important to note that we are only comparing intramolecular transamidation processes, which are relatively facile as compared to intermolecular ones. Thus, the dependence on the nature of the catalyst easily could be different for these two classes of this reaction.
20. For intramolecular Cu-catalyzed aryl amination reactions, see: Yamada, K.; Kubo, T.; Tokuyama, H.; Fukuyama, T. Synlett 2002, 231.
21. The stereochemistry of the product in Table 3, entry 3, was determined to be as shown by X-ray crystallography (see Supporting Information).