Palladium-catalyzed annulation of haloanilines and halobenzamides using norbornadiene as an acetylene synthon: a route to functionalized indolines, isoquinolinones, and indoles

Praew Thansandote; David G Hulcoop; Michael Langer; Mark Lautens

doi:10.1021/jo802604g

Palladium-catalyzed annulation of haloanilines and halobenzamides using norbornadiene as an acetylene synthon: a route to functionalized indolines, isoquinolinones, and indoles

J Org Chem. 2009 Feb 20;74(4):1673-8. doi: 10.1021/jo802604g.

Authors

Praew Thansandote¹, David G Hulcoop, Michael Langer, Mark Lautens

Affiliation

¹ Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.

PMID: 19143500
DOI: 10.1021/jo802604g

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylene / chemistry*
Aniline Compounds / chemistry*
Benzamides / chemistry*
Indoles / chemical synthesis*
Indoles / chemistry
Isoquinolines / chemical synthesis*
Isoquinolines / chemistry
Norbornanes / chemistry*
Palladium / chemistry*

Substances

Aniline Compounds
Benzamides
Indoles
Isoquinolines
Norbornanes
Palladium
indoline
isoquinoline
Acetylene
aniline
2,5-norbornadiene