An air-stable palladium/N-heterocyclic carbene complex and its reactivity in aryl amination

M S  Viciu; R M  Kissling; E D  Stevens; Steven Patrick Nolan

doi:10.1021/ol0260831

An air-stable palladium/N-heterocyclic carbene complex and its reactivity in aryl amination

M S Viciu, R M Kissling, E D Stevens, Steven Patrick Nolan

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249 Citations (Scopus)

Abstract

The synthesis and characterization of [Pd<IPr>Cl-2](2) (1), an air- and moisture-stable complex, is reported. The utilization of 1 as a catalyst for amination of aryl chlorides and bromides with a variety of amine coupling partners under mild conditions is described. The amination reactions with I show a remarkable insensitivity to oxygen and water, and thus the amination reactions could be performed in air on the benchtop with undried reagent grade solvents and substrates with small effects on reaction times and conversions.

Original language	English
Pages (from-to)	2229-2231
Number of pages	3
Journal	Organic Letters
Volume	4
Issue number	13
DOIs	https://doi.org/10.1021/ol0260831
Publication status	Published - 27 Jun 2002

Keywords

CROSS-COUPLING REACTIONS
CATALYZED AMINATION
ARYLBORONIC ACIDS
BOND FORMATION
C-N
CHLORIDES
CHLOROARENES
BROMIDES
LIGAND
SYSTEM

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title = "An air-stable palladium/N-heterocyclic carbene complex and its reactivity in aryl amination",

abstract = "The synthesis and characterization of [PdCl-2](2) (1), an air- and moisture-stable complex, is reported. The utilization of 1 as a catalyst for amination of aryl chlorides and bromides with a variety of amine coupling partners under mild conditions is described. The amination reactions with I show a remarkable insensitivity to oxygen and water, and thus the amination reactions could be performed in air on the benchtop with undried reagent grade solvents and substrates with small effects on reaction times and conversions.",

keywords = "CROSS-COUPLING REACTIONS, CATALYZED AMINATION, ARYLBORONIC ACIDS, BOND FORMATION, C-N, CHLORIDES, CHLOROARENES, BROMIDES, LIGAND, SYSTEM",

author = "Viciu, {M S} and Kissling, {R M} and Stevens, {E D} and Nolan, {Steven Patrick}",

year = "2002",

month = jun,

day = "27",

doi = "10.1021/ol0260831",

language = "English",

volume = "4",

pages = "2229--2231",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

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TY - JOUR

T1 - An air-stable palladium/N-heterocyclic carbene complex and its reactivity in aryl amination

AU - Viciu, M S

AU - Kissling, R M

AU - Stevens, E D

AU - Nolan, Steven Patrick

PY - 2002/6/27

Y1 - 2002/6/27

N2 - The synthesis and characterization of [PdCl-2](2) (1), an air- and moisture-stable complex, is reported. The utilization of 1 as a catalyst for amination of aryl chlorides and bromides with a variety of amine coupling partners under mild conditions is described. The amination reactions with I show a remarkable insensitivity to oxygen and water, and thus the amination reactions could be performed in air on the benchtop with undried reagent grade solvents and substrates with small effects on reaction times and conversions.

AB - The synthesis and characterization of [PdCl-2](2) (1), an air- and moisture-stable complex, is reported. The utilization of 1 as a catalyst for amination of aryl chlorides and bromides with a variety of amine coupling partners under mild conditions is described. The amination reactions with I show a remarkable insensitivity to oxygen and water, and thus the amination reactions could be performed in air on the benchtop with undried reagent grade solvents and substrates with small effects on reaction times and conversions.

KW - CROSS-COUPLING REACTIONS

KW - CATALYZED AMINATION

KW - ARYLBORONIC ACIDS

KW - BOND FORMATION

KW - C-N

KW - CHLORIDES

KW - CHLOROARENES

KW - BROMIDES

KW - LIGAND

KW - SYSTEM

U2 - 10.1021/ol0260831

DO - 10.1021/ol0260831

M3 - Article

SN - 1523-7060

VL - 4

SP - 2229

EP - 2231

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

An air-stable palladium/N-heterocyclic carbene complex and its reactivity in aryl amination

Abstract

Keywords

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