Unprecedented Negishi coupling at C-Br in the presence of a stannyl group as a convenient approach to pyridinylstannanes and their application in liquid crystal synthesis

被引：38

作者：

Getmanenko, Yulia A. ^{[1
]}

Twieg, Robert J. ^{[1
]}

机构：

[1] Kent State Univ, Dept Chem, Kent, OH 44242 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 03期

关键词：

D O I：

10.1021/jo701812t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The 2-bromo-5(or 6)-tri-n-butylstannylpyridines, prepared from dibromopyridines and i-PrMgCl at room temperature, undergo Negishi coupling with either alkyl or arylzinc chlorides. The new alkyl- and aryl-substituted pyridylstannanes produced are shown to be suitable for further functionalization by Stille coupling. A group of new liquid crystalline materials with aromatic cores comprised of pyridine and thiophene rings were prepared utilizing these new pyridinylstannanes as key intermediates.

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页码：830 / 839

页数：10

相关论文

共 35 条

[1]

[Anonymous], 1972, Inorg. Synth, DOI DOI 10.1002/9780470132449.CH23

[2]

BARROS MT, 2001, J CHEM SOC P1, V2, P166

[3] SELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED OLIGOTHIOPHENES [J].

BAUERLE, P ;

WURTHNER, F ;

GOTZ, G ;

EFFENBERGER, F .

SYNTHESIS-STUTTGART, 1993, (11) :1099-1103

[4] Synthesis of oligopyridines and their metal complexes as precursors to topological stereoisomers [J].

Benaglia, M ;

Ponzini, F ;

Woods, CR ;

Siegel, JS .

ORGANIC LETTERS, 2001, 3 (07) :967-969

[5] 2,3-diarylcyclopentenones as orally active, highly selective cyclooxygenase-2 inhibitors [J].

Black, WC ;

Brideau, C ;

Chan, CC ;

Charleson, S ;

Chauret, N ;

Claveau, D ;

Ethier, D ;

Gordon, R ;

Greig, G ;

Guay, J ;

Hughes, G ;

Jolicoeur, P ;

Leblanc, Y ;

Nicoll-Griffith, D ;

Ouimet, N ;

Riendeau, D ;

Visco, D ;

Wang, ZY ;

Xu, L ;

Prasit, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (07) :1274-1281

[6] Synthesis of substituted oligothiophenes and x-ray crystal structures of 3'-methyl-2,2':5',2''-terthiophene, 3,3''-dimethyl-2,2':5',2''-terthiophene and 5'-(2-thienyl)-2,2':3',2''-terthiophene [J].

Chaloner, PA ;

Gunatunga, SR ;

Hitchcock, PB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (08) :1597-1604

[7] Unusual C-6 lithiation of 2-chloropyridine-mediated by BuLi-Me2N(CH2)2OLi.: New access to 6-functional-2-chloropyridines and chloro-bis-heterocycles [J].

Choppin, S ;

Gros, P ;

Fort, Y .

ORGANIC LETTERS, 2000, 2 (06) :803-805

[8] First microwave-accelerated hiyama coupling of aryl- and vinylsiloxane derivatives: Clean cross-coupling of aryl chlorides within minutes [J].

Clarke, ML .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :303-307

[9]

Colasson BX, 2002, SYNLETT, P271

[10]

Frahn J, 1997, SYNTHESIS-STUTTGART, P1301

← 1 2 3 4 →