Palladium-catalyzed annulation of haloanilines and halobenzamides using norbornadiene as an acetylene synthon: a route to functionalized indolines, isoquinolinones, and indoles.
A general procedure for the palladium-catalyzed annulation of substituted haloanilines with norbornadiene gives functionalized indolines in 51-98% yield. These indolines can be rapidly converted to benzenoid-substituted indoles and tricyclic indolines. Extension to the use of substituted halobenzamides gives functionalized isoquinolinones in up to 86% yield.
Thansandote
Praew
P
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
Hulcoop
David G
DG
Langer
Michael
M
Lautens
Mark
M
D000114:Acetylene / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D001549:Benzamides / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D009636:Norbornanes / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
D000814:Aniline Compounds; D001549:Benzamides; D007211:Indoles; D007546:Isoquinolines; D009636:Norbornanes; D010165:Palladium; C057812:indoline; C039109:isoquinoline; D000114:Acetylene; C023650:aniline; C048294:2,5-norbornadiene