A palladium-catalyzed alkylation/direct arylation synthesis of nitrogen-containing heterocycles.
A norbornene-mediated palladium-catalyzed sequence is described in which an alkyl-aryl bond and an aryl-heteroaryl bond are formed in one reaction vessel. The aryl-heteroaryl bond-forming step occurs via a direct arylation reaction. A number of six-, seven-, and eight-membered ring-annulated indoles, pyrroles, pyrazoles, and azaindoles were synthesized from the corresponding bromoalkyl azole and an aryl iodide.
Blaszykowski
Christophe
C
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada.
Aktoudianakis
Evangelos
E
Alberico
Dino
D
Bressy
Cyril
C
Hulcoop
David G
DG
Jafarpour
Farnaz
F
Joushaghani
Arash
A
Laleu
Benoît
B
Lautens
Mark
M
D000478:Alkylation; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
D006571:Heterocyclic Compounds; D010165:Palladium; D009584:Nitrogen