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Base effect and inhibition of catalytic activity in palladium-catalyzed N-heteroarylation of pyrazoles with 2,6-dibromopyridine
Sun, XJ; Yu, ZK; Wu, SH; Xiao, WJ
Source PublicationORGANOMETALLICS
2005-06-06
DOI10.1021/om0501576
Volume24Issue:12Pages:2959-2963
Indexed BySCI ; IC
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Inorganic & Nuclear ; Chemistry, Organic
WOS Research AreaChemistry
WOS KeywordNITROGEN BOND FORMATION ; ARYL HALIDES ; METAL-COMPLEXES ; C-N ; ARYLATION ; AMINATION ; CHEMISTRY ; LIGANDS ; ARYLAMINES ; HETEROATOM
AbstractUsing the catalytic system Pd(OAc)(2)/PPh3, coupling of 2,6-dibromopyridine (1) and pyrazoles (2) in a molar ratio of 1:2:base = 1:2.4:2.5 afforded the monosubstituted compounds 3 as the major products when KOtBu was used as the base. Without using the catalyst or using NaOtBu as the base the disubstituted compounds 4 were formed as the major products in yields up to 93%. Reactions of 1 and 2 in a molar ratio of 1:2:base = 1:1:1 selectively produced compounds 3 in yields up to 82% when KOtBu was used as the base. The complex from the reaction of 3 and Pd(OAc)(2) did not undergo further reaction with 1 to form 4 in the presence of a base. The base effect and inhibition of catalytic activity for Pd(OAc)(2) are discussed.
Language英语
WOS IDWOS:000229574600017
Citation statistics
Cited Times:45[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/139634
Collection中国科学院大连化学物理研究所
Affiliation1.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
2.Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide, Wuhan 430007, Peoples R China
Recommended Citation
GB/T 7714
Sun, XJ,Yu, ZK,Wu, SH,et al. Base effect and inhibition of catalytic activity in palladium-catalyzed N-heteroarylation of pyrazoles with 2,6-dibromopyridine[J]. ORGANOMETALLICS,2005,24(12):2959-2963.
APA Sun, XJ,Yu, ZK,Wu, SH,&Xiao, WJ.(2005).Base effect and inhibition of catalytic activity in palladium-catalyzed N-heteroarylation of pyrazoles with 2,6-dibromopyridine.ORGANOMETALLICS,24(12),2959-2963.
MLA Sun, XJ,et al."Base effect and inhibition of catalytic activity in palladium-catalyzed N-heteroarylation of pyrazoles with 2,6-dibromopyridine".ORGANOMETALLICS 24.12(2005):2959-2963.
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