Suzuki-Miyaura, alpha-ketone arylation and dehalogenation reactions catalyzed by a versatile N-heterocyclic carbene-palladacycle complex

O Navarro; N Marion; Y Oonishi; RA Kelly; Steven Patrick Nolan

doi:10.1021/jo0521201

Suzuki-Miyaura, alpha-ketone arylation and dehalogenation reactions catalyzed by a versatile N-heterocyclic carbene-palladacycle complex

O Navarro, N Marion, Y Oonishi, RA Kelly, Steven Patrick Nolan

Research output: Contribution to journal › Article › peer-review

Abstract

[GRAPHICS]

The activity of the complex (IPr)PdCl(eta(2)-N,C-C12H7NMe2), 1 [IPr = (N,N'-bis(2,6-diisopropylphenyl)-imidazol)-2-ylidene], in the Suzuki-Miyaura cross-coupling reaction involving unactivated aryl chlorides and triflates with arylboronic acids at room temperature in technical, grade 2-propanol is described. These conditions allow for the synthesis of di- and tri-ortho-substituted biaryls in very short reaction times. This complex also displays very high activity for (x-ketone arylation and dehalogenation reactions of activated and unactivated aryl chlorides.

Original language	English
Pages (from-to)	685-692
Number of pages	8
Journal	The Journal of Organic Chemistry
Volume	71
Issue number	2
DOIs	https://doi.org/10.1021/jo0521201
Publication status	Published - 20 Jan 2006

Keywords

CROSS-COUPLING REACTION
HIGHLY EFFICIENT CATALYSTS
BOND-FORMING REACTIONS
ARYL CHLORIDES
C-C
TRIARYLPHOSPHITE COMPLEXES
ROOM-TEMPERATURE
NUCLEOPHILIC CARBENES
PHOSPHINITE COMPLEXES
PALLADIUM CATALYSTS

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10.1021/jo0521201

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@article{035c6406cf264ecf96f8b6b18481c0ee,

title = "Suzuki-Miyaura, alpha-ketone arylation and dehalogenation reactions catalyzed by a versatile N-heterocyclic carbene-palladacycle complex",

abstract = "[GRAPHICS]The activity of the complex (IPr)PdCl(eta(2)-N,C-C12H7NMe2), 1 [IPr = (N,N'-bis(2,6-diisopropylphenyl)-imidazol)-2-ylidene], in the Suzuki-Miyaura cross-coupling reaction involving unactivated aryl chlorides and triflates with arylboronic acids at room temperature in technical, grade 2-propanol is described. These conditions allow for the synthesis of di- and tri-ortho-substituted biaryls in very short reaction times. This complex also displays very high activity for (x-ketone arylation and dehalogenation reactions of activated and unactivated aryl chlorides.",

keywords = "CROSS-COUPLING REACTION, HIGHLY EFFICIENT CATALYSTS, BOND-FORMING REACTIONS, ARYL CHLORIDES, C-C, TRIARYLPHOSPHITE COMPLEXES, ROOM-TEMPERATURE, NUCLEOPHILIC CARBENES, PHOSPHINITE COMPLEXES, PALLADIUM CATALYSTS",

author = "O Navarro and N Marion and Y Oonishi and RA Kelly and Nolan, {Steven Patrick}",

year = "2006",

month = jan,

day = "20",

doi = "10.1021/jo0521201",

language = "English",

volume = "71",

pages = "685--692",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society (ACS)",

number = "2",

}

TY - JOUR

T1 - Suzuki-Miyaura, alpha-ketone arylation and dehalogenation reactions catalyzed by a versatile N-heterocyclic carbene-palladacycle complex

AU - Navarro, O

AU - Marion, N

AU - Oonishi, Y

AU - Kelly, RA

AU - Nolan, Steven Patrick

PY - 2006/1/20

Y1 - 2006/1/20

N2 - [GRAPHICS]The activity of the complex (IPr)PdCl(eta(2)-N,C-C12H7NMe2), 1 [IPr = (N,N'-bis(2,6-diisopropylphenyl)-imidazol)-2-ylidene], in the Suzuki-Miyaura cross-coupling reaction involving unactivated aryl chlorides and triflates with arylboronic acids at room temperature in technical, grade 2-propanol is described. These conditions allow for the synthesis of di- and tri-ortho-substituted biaryls in very short reaction times. This complex also displays very high activity for (x-ketone arylation and dehalogenation reactions of activated and unactivated aryl chlorides.

AB - [GRAPHICS]The activity of the complex (IPr)PdCl(eta(2)-N,C-C12H7NMe2), 1 [IPr = (N,N'-bis(2,6-diisopropylphenyl)-imidazol)-2-ylidene], in the Suzuki-Miyaura cross-coupling reaction involving unactivated aryl chlorides and triflates with arylboronic acids at room temperature in technical, grade 2-propanol is described. These conditions allow for the synthesis of di- and tri-ortho-substituted biaryls in very short reaction times. This complex also displays very high activity for (x-ketone arylation and dehalogenation reactions of activated and unactivated aryl chlorides.

KW - CROSS-COUPLING REACTION

KW - HIGHLY EFFICIENT CATALYSTS

KW - BOND-FORMING REACTIONS

KW - ARYL CHLORIDES

KW - C-C

KW - TRIARYLPHOSPHITE COMPLEXES

KW - ROOM-TEMPERATURE

KW - NUCLEOPHILIC CARBENES

KW - PHOSPHINITE COMPLEXES

KW - PALLADIUM CATALYSTS

UR - http://www.scopus.com/inward/record.url?scp=30744453567&partnerID=8YFLogxK

U2 - 10.1021/jo0521201

DO - 10.1021/jo0521201

M3 - Article

SN - 0022-3263

VL - 71

SP - 685

EP - 692

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 2

ER -

Suzuki-Miyaura, alpha-ketone arylation and dehalogenation reactions catalyzed by a versatile N-heterocyclic carbene-palladacycle complex

Abstract

Keywords

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