Direct C5-arylation reaction between imidazoles and aryl chlorides catalyzed by palladium complexes with phosphines and N-heterocyclic carbenes

P. Vijaya Kumar; Wu Shien Lin; Jiun Shian Shen; Debkumar Nandi; Hon Man Lee

doi:10.1021/om200490k

Direct C5-arylation reaction between imidazoles and aryl chlorides catalyzed by palladium complexes with phosphines and N-heterocyclic carbenes

P. Vijaya Kumar, Wu Shien Lin, Jiun Shian Shen, Debkumar Nandi, Hon Man Lee

Department of Chemistry

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

77 Citations (Scopus)

Abstract

Palladium(II) acetate complexes bearing phosphines and carbene ligands, Pd(L)(PR₃)(OAc)₂ (1a, R = Ph; 1b, R = Cy; L = 1,3-dibenzylimidazol-2-ylidene), were prepared by salt metathesis reactions of their chloro complexes with AgOAc in good yields. The electron-rich 1b was efficient in catalyzing C-5 direct arylation of imidazoles with aryl halides. Most significantly, the catalytic system allows a range of aryl chlorides as substrates. Microwave irradiation effectively promotes the reactions, with good yields obtainable in only 2 h. In combination with the classical method of C-C bond formation reactions, novel imidazole derivatives featuring biaryl and styryl subunits were successfully obtained from 1,4-dichlorobenzene and 1-bromo-4-chlorobenzene.

Original language	English
Pages (from-to)	5160-5169
Number of pages	10
Journal	Organometallics
Volume	30
Issue number	19
DOIs	https://doi.org/10.1021/om200490k
Publication status	Published - 2011 Oct 10

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Direct C5-arylation reaction between imidazoles and aryl chlorides catalyzed by palladium complexes with phosphines and N-heterocyclic carbenes",

abstract = "Palladium(II) acetate complexes bearing phosphines and carbene ligands, Pd(L)(PR3)(OAc)2 (1a, R = Ph; 1b, R = Cy; L = 1,3-dibenzylimidazol-2-ylidene), were prepared by salt metathesis reactions of their chloro complexes with AgOAc in good yields. The electron-rich 1b was efficient in catalyzing C-5 direct arylation of imidazoles with aryl halides. Most significantly, the catalytic system allows a range of aryl chlorides as substrates. Microwave irradiation effectively promotes the reactions, with good yields obtainable in only 2 h. In combination with the classical method of C-C bond formation reactions, novel imidazole derivatives featuring biaryl and styryl subunits were successfully obtained from 1,4-dichlorobenzene and 1-bromo-4-chlorobenzene.",

author = "Kumar, {P. Vijaya} and Lin, {Wu Shien} and Shen, {Jiun Shian} and Debkumar Nandi and Lee, {Hon Man}",

year = "2011",

month = oct,

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doi = "10.1021/om200490k",

language = "English",

volume = "30",

pages = "5160--5169",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Direct C5-arylation reaction between imidazoles and aryl chlorides catalyzed by palladium complexes with phosphines and N-heterocyclic carbenes

AU - Kumar, P. Vijaya

AU - Lin, Wu Shien

AU - Shen, Jiun Shian

AU - Nandi, Debkumar

AU - Lee, Hon Man

PY - 2011/10/10

Y1 - 2011/10/10

N2 - Palladium(II) acetate complexes bearing phosphines and carbene ligands, Pd(L)(PR3)(OAc)2 (1a, R = Ph; 1b, R = Cy; L = 1,3-dibenzylimidazol-2-ylidene), were prepared by salt metathesis reactions of their chloro complexes with AgOAc in good yields. The electron-rich 1b was efficient in catalyzing C-5 direct arylation of imidazoles with aryl halides. Most significantly, the catalytic system allows a range of aryl chlorides as substrates. Microwave irradiation effectively promotes the reactions, with good yields obtainable in only 2 h. In combination with the classical method of C-C bond formation reactions, novel imidazole derivatives featuring biaryl and styryl subunits were successfully obtained from 1,4-dichlorobenzene and 1-bromo-4-chlorobenzene.

AB - Palladium(II) acetate complexes bearing phosphines and carbene ligands, Pd(L)(PR3)(OAc)2 (1a, R = Ph; 1b, R = Cy; L = 1,3-dibenzylimidazol-2-ylidene), were prepared by salt metathesis reactions of their chloro complexes with AgOAc in good yields. The electron-rich 1b was efficient in catalyzing C-5 direct arylation of imidazoles with aryl halides. Most significantly, the catalytic system allows a range of aryl chlorides as substrates. Microwave irradiation effectively promotes the reactions, with good yields obtainable in only 2 h. In combination with the classical method of C-C bond formation reactions, novel imidazole derivatives featuring biaryl and styryl subunits were successfully obtained from 1,4-dichlorobenzene and 1-bromo-4-chlorobenzene.

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