Synthesis of benzannulated N-heterocycles by a palladium-catalyzed C-C/C-N coupling of bromoalkylamines

Praew Thansandote; Manuel Raemy; Alena Rudolph; Mark Lautens

doi:10.1021/ol702472u

Synthesis of benzannulated N-heterocycles by a palladium-catalyzed C-C/C-N coupling of bromoalkylamines

Org Lett. 2007 Dec 6;9(25):5255-8. doi: 10.1021/ol702472u. Epub 2007 Nov 15.

Authors

Praew Thansandote¹, Manuel Raemy, Alena Rudolph, Mark Lautens

Affiliation

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

PMID: 18001046
DOI: 10.1021/ol702472u

Abstract

A palladium-catalyzed domino intermolecular alkylation/intramolecular amination of functionalized aryl iodides represents a new strategy for the synthesis of benzannulated N-heterocycles, affording functionalized indolines and tetrahydroquinolines from simple precursors.

Publication types

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

MeSH terms

Alkylation
Amines / chemistry*
Benzene / chemistry*
Bromine Compounds / chemistry*
Carbon / chemistry*
Catalysis
Heterocyclic Compounds / chemical synthesis*
Heterocyclic Compounds / chemistry
Hydroquinones / chemistry
Indoles / chemistry
Molecular Structure
Nitrogen / chemistry*
Palladium / chemistry*

Substances

Amines
Bromine Compounds
Heterocyclic Compounds
Hydroquinones
Indoles
Palladium
Carbon
Benzene
Nitrogen
hydroquinone