(IPr)Pd(acac)Cl: An easily synthesized, efficient, and versatile precatalyst for C-N and C-C bond formation

N Marion; EC Ecarnot; O Navarro; D Amoroso; A Bell; Steven Patrick Nolan

doi:10.1021/jo060190h

(IPr)Pd(acac)Cl: An easily synthesized, efficient, and versatile precatalyst for C-N and C-C bond formation

N Marion, EC Ecarnot, O Navarro, D Amoroso, A Bell, Steven Patrick Nolan

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

178 Citations (Scopus)

Abstract

A very straightforward synthesis of (IPr) Pd(acac)Cl from two commercially available starting materials, Pd(acac)(2) and IPr center dot HCl [acac = acetylacetonate; IPr = N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], has been developed. The resulting complex, ( IPr) Pd( acac) Cl ( 1), has proven to be a highly active Pd-II precatalyst in the Buchwald-Hartwig and the alpha-ketone arylation reactions. A wide range of substrates has been screened, including unactivated, sterically hindered, and heterocyclic aryl chlorides.

Original language	English
Pages (from-to)	3816-3821
Number of pages	6
Journal	The Journal of Organic Chemistry
Volume	71
Issue number	10
DOIs	https://doi.org/10.1021/jo060190h
Publication status	Published - 12 May 2006

Keywords

n
PALLADIUM-CATALYZED AMINATION
CROSS-COUPLING REACTIONS
ALPHA-ARYLATION
ARYL CHLORIDES
ELECTRON-TRANSFER
ENERGY-TRANSFER
BROMIDES
LIGAND
KETONES
ARYLAMINES

Access to Document

10.1021/jo060190h

Cite this

@article{a05958c89ff146fcb11b67d6935ddd10,

title = "(IPr)Pd(acac)Cl: An easily synthesized, efficient, and versatile precatalyst for C-N and C-C bond formation",

abstract = "A very straightforward synthesis of (IPr) Pd(acac)Cl from two commercially available starting materials, Pd(acac)(2) and IPr center dot HCl [acac = acetylacetonate; IPr = N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], has been developed. The resulting complex, ( IPr) Pd( acac) Cl ( 1), has proven to be a highly active Pd-II precatalyst in the Buchwald-Hartwig and the alpha-ketone arylation reactions. A wide range of substrates has been screened, including unactivated, sterically hindered, and heterocyclic aryl chlorides.",

keywords = "n, PALLADIUM-CATALYZED AMINATION, CROSS-COUPLING REACTIONS, ALPHA-ARYLATION, ARYL CHLORIDES, ELECTRON-TRANSFER, ENERGY-TRANSFER, BROMIDES, LIGAND, KETONES, ARYLAMINES",

author = "N Marion and EC Ecarnot and O Navarro and D Amoroso and A Bell and Nolan, {Steven Patrick}",

year = "2006",

month = may,

day = "12",

doi = "10.1021/jo060190h",

language = "English",

volume = "71",

pages = "3816--3821",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society (ACS)",

number = "10",

}

TY - JOUR

T1 - (IPr)Pd(acac)Cl: An easily synthesized, efficient, and versatile precatalyst for C-N and C-C bond formation

AU - Marion, N

AU - Ecarnot, EC

AU - Navarro, O

AU - Amoroso, D

AU - Bell, A

AU - Nolan, Steven Patrick

PY - 2006/5/12

Y1 - 2006/5/12

N2 - A very straightforward synthesis of (IPr) Pd(acac)Cl from two commercially available starting materials, Pd(acac)(2) and IPr center dot HCl [acac = acetylacetonate; IPr = N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], has been developed. The resulting complex, ( IPr) Pd( acac) Cl ( 1), has proven to be a highly active Pd-II precatalyst in the Buchwald-Hartwig and the alpha-ketone arylation reactions. A wide range of substrates has been screened, including unactivated, sterically hindered, and heterocyclic aryl chlorides.

AB - A very straightforward synthesis of (IPr) Pd(acac)Cl from two commercially available starting materials, Pd(acac)(2) and IPr center dot HCl [acac = acetylacetonate; IPr = N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], has been developed. The resulting complex, ( IPr) Pd( acac) Cl ( 1), has proven to be a highly active Pd-II precatalyst in the Buchwald-Hartwig and the alpha-ketone arylation reactions. A wide range of substrates has been screened, including unactivated, sterically hindered, and heterocyclic aryl chlorides.

KW - n

KW - PALLADIUM-CATALYZED AMINATION

KW - CROSS-COUPLING REACTIONS

KW - ALPHA-ARYLATION

KW - ARYL CHLORIDES

KW - ELECTRON-TRANSFER

KW - ENERGY-TRANSFER

KW - BROMIDES

KW - LIGAND

KW - KETONES

KW - ARYLAMINES

UR - http://www.scopus.com/inward/record.url?scp=33646498964&partnerID=8YFLogxK

U2 - 10.1021/jo060190h

DO - 10.1021/jo060190h

M3 - Article

SN - 0022-3263

VL - 71

SP - 3816

EP - 3821

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 10

ER -

(IPr)Pd(acac)Cl: An easily synthesized, efficient, and versatile precatalyst for C-N and C-C bond formation

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this