Comparison between PdCl2(PPh3)2- and NiCl2(PPh3)2-catalyzed cross-coupling of aryl halides by intramolecularly stabilized dialkylaluminum reagents

D. Gelman; G. Höhne; H. Schumann; J. Blum

doi:10.1055/s-2001-12364

Comparison between PdCl₂(PPh₃)₂- and NiCl₂(PPh₃)₂-catalyzed cross-coupling of aryl halides by intramolecularly stabilized dialkylaluminum reagents

D. Gelman, G. Höhne, H. Schumann^*, J. Blum

^*Corresponding author for this work

Institute of Chemistry

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

15 Scopus citations

Abstract

The catalytic activities of PdCl₂(PPh₃)₂ and of NiCl₂(PPh₃)₂ in cross coupling of some chloro- and bromoarenes with intramolecularly stabilized aluminum complexes [R₂AlOCH₂CH₂NMe₂]₂ (R = Ph, PhC≡C, PhCH₂, Et and i-Bu) are compared. The palladium catalyst promotes clean cross-alkylation of aryl bromides indifferently to the nature of the R groups of the alkylating reagents, but does not activate aryl chlorides. The nickel complex catalyzes cross-alkylation of both aryl bromides and chlorides, provided the R groups do not have β-hydrogen atoms. Diethyl- and diisobutylaluminum complexes that disproportionate in the presence of the nickel catalyst cause substantial hydrogenolysis of the aryl halides.

Original language	English
Pages (from-to)	591-594
Number of pages	4
Journal	Synthesis
Issue number	4
DOIs	https://doi.org/10.1055/s-2001-12364
State	Published - 2001

Keywords

Aluminum complexes
Aryl halides
Cross coupling
Nickel catalyst
Palladium catalyst

Access to Document

10.1055/s-2001-12364

Cite this

@article{c5fb5dacba7d4c09bb52e5395cb06681,

title = "Comparison between PdCl2(PPh3)2- and NiCl2(PPh3)2-catalyzed cross-coupling of aryl halides by intramolecularly stabilized dialkylaluminum reagents",

abstract = "The catalytic activities of PdCl2(PPh3)2 and of NiCl2(PPh3)2 in cross coupling of some chloro- and bromoarenes with intramolecularly stabilized aluminum complexes [R2AlOCH2CH2NMe2]2 (R = Ph, PhC≡C, PhCH2, Et and i-Bu) are compared. The palladium catalyst promotes clean cross-alkylation of aryl bromides indifferently to the nature of the R groups of the alkylating reagents, but does not activate aryl chlorides. The nickel complex catalyzes cross-alkylation of both aryl bromides and chlorides, provided the R groups do not have β-hydrogen atoms. Diethyl- and diisobutylaluminum complexes that disproportionate in the presence of the nickel catalyst cause substantial hydrogenolysis of the aryl halides.",

keywords = "Aluminum complexes, Aryl halides, Cross coupling, Nickel catalyst, Palladium catalyst",

author = "D. Gelman and G. H{\"o}hne and H. Schumann and J. Blum",

year = "2001",

doi = "10.1055/s-2001-12364",

language = "אנגלית",

pages = "591--594",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "4",

}

TY - JOUR

T1 - Comparison between PdCl2(PPh3)2- and NiCl2(PPh3)2-catalyzed cross-coupling of aryl halides by intramolecularly stabilized dialkylaluminum reagents

AU - Gelman, D.

AU - Höhne, G.

AU - Schumann, H.

AU - Blum, J.

PY - 2001

Y1 - 2001

N2 - The catalytic activities of PdCl2(PPh3)2 and of NiCl2(PPh3)2 in cross coupling of some chloro- and bromoarenes with intramolecularly stabilized aluminum complexes [R2AlOCH2CH2NMe2]2 (R = Ph, PhC≡C, PhCH2, Et and i-Bu) are compared. The palladium catalyst promotes clean cross-alkylation of aryl bromides indifferently to the nature of the R groups of the alkylating reagents, but does not activate aryl chlorides. The nickel complex catalyzes cross-alkylation of both aryl bromides and chlorides, provided the R groups do not have β-hydrogen atoms. Diethyl- and diisobutylaluminum complexes that disproportionate in the presence of the nickel catalyst cause substantial hydrogenolysis of the aryl halides.

AB - The catalytic activities of PdCl2(PPh3)2 and of NiCl2(PPh3)2 in cross coupling of some chloro- and bromoarenes with intramolecularly stabilized aluminum complexes [R2AlOCH2CH2NMe2]2 (R = Ph, PhC≡C, PhCH2, Et and i-Bu) are compared. The palladium catalyst promotes clean cross-alkylation of aryl bromides indifferently to the nature of the R groups of the alkylating reagents, but does not activate aryl chlorides. The nickel complex catalyzes cross-alkylation of both aryl bromides and chlorides, provided the R groups do not have β-hydrogen atoms. Diethyl- and diisobutylaluminum complexes that disproportionate in the presence of the nickel catalyst cause substantial hydrogenolysis of the aryl halides.

KW - Aluminum complexes

KW - Aryl halides

KW - Cross coupling

KW - Nickel catalyst

KW - Palladium catalyst

UR - http://www.scopus.com/inward/record.url?scp=0035067483&partnerID=8YFLogxK

U2 - 10.1055/s-2001-12364

DO - 10.1055/s-2001-12364

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:0035067483

SN - 0039-7881

SP - 591

EP - 594

JO - Synthesis

JF - Synthesis

IS - 4

ER -

Comparison between PdCl₂(PPh₃)₂- and NiCl₂(PPh₃)₂-catalyzed cross-coupling of aryl halides by intramolecularly stabilized dialkylaluminum reagents

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this