Palladium-catalyzed aryl amination-heck cyclization cascade: A one-flask approach to 3-substituted Indoles

Thomas Jensen; Henrik Pedersen; B. Bang-Andersen; Robert Madsen; Morten Jørgensen

doi:10.1002/anie.200703763

Palladium-catalyzed aryl amination-heck cyclization cascade: A one-flask approach to 3-substituted Indoles

Thomas Jensen
, Henrik Pedersen
, B. Bang-Andersen
, Robert Madsen
, Morten Jørgensen

Department of Chemistry

H. Lundbeck A/S

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Two for the price of one: A Pd/dppf-based catalyst provides access to the title compounds from 1,2-dihalogenated aromatic compounds and allylic amines in a single reaction flask. The initial aryl amination step occurs with excellent selectivity for the aryl iodide to ensure the formation of a single indole regioisomer, which can be functionalized in situ by N-arylation (see scheme).

Original language	English
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	5
Pages (from-to)	888-890
ISSN	1433-7851
DOIs	https://doi.org/10.1002/anie.200703763
Publication status	Published - 2008

Keywords

palladium
amination
indoles
phosphane ligands
Heck reaction

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abstract = "Two for the price of one: A Pd/dppf-based catalyst provides access to the title compounds from 1,2-dihalogenated aromatic compounds and allylic amines in a single reaction flask. The initial aryl amination step occurs with excellent selectivity for the aryl iodide to ensure the formation of a single indole regioisomer, which can be functionalized in situ by N-arylation (see scheme). ",

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AU - Jensen, Thomas

AU - Pedersen, Henrik

AU - Bang-Andersen, B.

AU - Madsen, Robert

AU - Jørgensen, Morten

PY - 2008

Y1 - 2008

N2 - Two for the price of one: A Pd/dppf-based catalyst provides access to the title compounds from 1,2-dihalogenated aromatic compounds and allylic amines in a single reaction flask. The initial aryl amination step occurs with excellent selectivity for the aryl iodide to ensure the formation of a single indole regioisomer, which can be functionalized in situ by N-arylation (see scheme).

AB - Two for the price of one: A Pd/dppf-based catalyst provides access to the title compounds from 1,2-dihalogenated aromatic compounds and allylic amines in a single reaction flask. The initial aryl amination step occurs with excellent selectivity for the aryl iodide to ensure the formation of a single indole regioisomer, which can be functionalized in situ by N-arylation (see scheme).

KW - palladium

KW - amination

KW - indoles

KW - phosphane ligands

KW - Heck reaction

U2 - 10.1002/anie.200703763

DO - 10.1002/anie.200703763

M3 - Journal article

C2 - 18081116

SN - 1433-7851

VL - 47

SP - 888

EP - 890

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 5

ER -

Palladium-catalyzed aryl amination-heck cyclization cascade: A one-flask approach to 3-substituted Indoles

Abstract

Keywords

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