Direct synthesis of heteroarylethynes via palladium-catalyzed coupling of heteroaryl halides with ethynylzinc halides. Its application to an efficient synthesis of a thiophenelactone from Chamaemelum nobile L

被引:30
作者
Negishi, E [1 ]
Xu, CD [1 ]
Tan, Z [1 ]
Kotora, M [1 ]
机构
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
关键词
D O I
10.3987/COM-97-S79
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of terminal alkynes containing a heteroaryl group can be directly and selectively synthesized by the Pd-catalyzed coupling of heteroaryl iodides or bromides with ethynylzinc halides. Various compounds of this class containing furan, thiophene, and pyridine have been prepared, and the procedure has been applied to an efficient and selective synthesis of a thiophenelactone from Chamaemelum nobile L.
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页码:209 / 214
页数:6
相关论文
共 14 条
[1]  
AMES DE, 1981, SYNTHESIS-STUTTGART, P364
[2]   SYNTHESIS OF 3,2'-5',3'-TERTHIOPHENE AND OTHER TERTHIOPHENES BY THE THIOPHENECARBOXALDEHYDE-]ETHYNYLTHIOPHENE-]DITHIENYLBUTADIYNE ROUTE [J].
BENY, JP ;
DHAWAN, SN ;
KAGAN, J ;
SUNDLASS, S .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11) :2201-2204
[3]   POLYACETYLENVERBINDUNGEN .IC. UBER EIN THIOPHENLACTON AUS CHAMAEMELUM NOBILE L [J].
BOHLMANN, F ;
ZDERO, C .
CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (04) :1226-&
[4]   HIGHLY GENERAL STEREO-SELECTIVE, REGIO-SELECTIVE, AND CHEMO-SELECTIVE SYNTHESIS OF TERMINAL AND INTERNAL CONJUGATED ENYNES BY PD-CATALYSED REACTION OF ALKYNYLZINC REAGENTS WITH ALKENYL HALIDES [J].
KING, AO ;
OKUKADO, N ;
NEGISHI, EI .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (19) :683-684
[5]   GENERAL SYNTHESIS OF TERMINAL AND INTERNAL ARYLALKYNES BY PALLADIUM-CATALYZED REACTION OF ALKYNYLZINC REAGENTS WITH ARYL HALIDES [J].
KING, AO ;
NEGISHI, EI ;
VILLANI, FJ ;
SILVEIRA, A .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (02) :358-360
[6]  
Kotora M, 1997, SYNTHESIS-STUTTGART, P121
[7]   A CONVENIENT SYNTHESIS OF GAMMA-(Z)-ALKYLIDENE BUTENOLIDES [J].
LU, XY ;
HUANG, XL ;
MA, SM .
TETRAHEDRON LETTERS, 1993, 34 (37) :5963-5966
[8]  
MINNIS W, 1943, ORG SYNTH COLL, V2, P357
[9]  
Negishi E., 1978, ASPECTS MECH ORGANOM, P285, DOI DOI 10.1007/978-1-4684-3393-7_12
[10]  
NEGISHI E, UNPUB SYNLETT