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 | |
| Publication status | Published - 2011 Oct 10 |
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All Science Journal Classification (ASJC) codes
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
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Direct C5-arylation reaction between imidazoles and aryl chlorides catalyzed by palladium complexes with phosphines and N-heterocyclic carbenes. / Kumar, P. Vijaya; Lin, Wu Shien; Shen, Jiun Shian; Nandi, Debkumar; Lee, Hon Man.
In: Organometallics, Vol. 30, No. 19, 10.10.2011, p. 5160-5169.Research output: Contribution to journal › Article
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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U2 - 10.1021/om200490k
DO - 10.1021/om200490k
M3 - Article
AN - SCOPUS:80053550775
VL - 30
SP - 5160
EP - 5169
JO - Organometallics
JF - Organometallics
SN - 0276-7333
IS - 19
ER -