A SYNTHESIS OF SUBSTITUTED 2-PYRONES BY CARBONYLATIVE CROSS-COUPLING-THERMOLYSIS OF 4-HALOCYCLOBUTENONES WITH ALKENYLSTANNANE, ARYLSTANNANE, AND HETEROARYLSTANNANE

被引:42
作者
LIEBESKIND, LS
WANG, JY
机构
[1] Department of Chemistry, Emory University Atlanta
关键词
D O I
10.1016/S0040-4020(01)87262-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium catalyzed carbonylative cross-coupling of 4-chloro-2,3-disubstituted-2-cyclobutenones with alkenyl-, aryl-, and heteroaryltin reagents and thermolysis provides a general method for the synthesis of 2,3,6-trisubstituted-2-pyrones. The reaction is regiospecific, coupling occurring preferentially at the 4-position of the cyclobutenone.
引用
收藏
页码:5461 / 5470
页数:10
相关论文
共 40 条
[31]   PALLADIUM CATALYZED COUPLING OF ORGANOTIN REAGENTS WITH ORGANIC ELECTROPHILES [J].
STILLE, JK .
PURE AND APPLIED CHEMISTRY, 1985, 57 (12) :1771-1780
[32]   THE PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOTIN REAGENTS WITH ORGANIC ELECTROPHILES [J].
STILLE, JK .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (06) :508-523
[33]   ACID-CATALYZED RING EXPANSION OF 1-(1-METHOXY-1,2-PROPADIENYL)-2-CYCLOBUTEN-1-OLS - SYNTHESIS OF 5-HYDROXY-5-VINYL-2-CYCLOPENTEN-1-ONES AND THEIR STEREOSELECTIVE TRANSFORMATION TO 5-(2-ACETOXYETHYLIDENE)-2-CYCLOPENTEN-1-ONES [J].
STONE, GB ;
LIEBESKIND, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4614-4622
[34]   NICKEL(0)-CATALYZED NOVEL COOLIGOMERIZATION OF ETHOXY(TRIMETHYLSILYL)ETHYNE WITH CARBON-DIOXIDE TO 4,6-DIETHOXY-3-[1-ETHOXY-2,2-BIS(TRIMETHYLSILYL)VINYL]-5-(TRIMETHYLSILYL)-2-PYRONE [J].
TSUDA, T ;
HASEGAWA, N ;
SAEGUSA, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (13) :945-947
[35]   FUNCTIONALIZED PHOSPHINE-LIGANDS IN TRANSITION METAL-CATALYZED ORGANIC-SYNTHESIS - NICKEL(0)-CATALYZED CYCLO-ADDITION OF TERMINALLY UNSUBSTITUTED DIYNES AND CARBON-DIOXIDE TO BICYCLIC 2-PYRONES [J].
TSUDA, T ;
MORIKAWA, S ;
SAEGUSA, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (01) :9-10
[36]   NICKEL(0)-CATALYZED CYCLO-ADDITION OF DIYNES AND CARBON-DIOXIDE TO BICYCLIC ALPHA-PYRONES [J].
TSUDA, T ;
MORIKAWA, S ;
SUMIYA, R ;
SAEGUSA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3140-3145
[37]   CYERCENES, NOVEL POLYPROPIONATE PYRONES FROM THE AUTOTOMIZING MEDITERRANEAN MOLLUSK CYERCE-CRISTALLINA [J].
VARDARO, RR ;
DIMARZO, V ;
CRISPINO, A ;
CIMINO, G .
TETRAHEDRON, 1991, 47 (29) :5569-5576
[38]   ACTIVATION OF CO2 ON TRANSITION-METAL CENTERS - COURSE OF HOMOGENEOUS-CATALYTIC FORMATION OF 2-PYRONE FROM CARBON-DIOXIDE AND HEX-3-YNE ON NICKEL(0) FRAGMENTS [J].
WALTHER, D ;
BRAUNLICH, G ;
KEMPE, R ;
SIELER, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 436 (01) :109-119
[39]   REACTIONS OF AROMATIC SULFENYL COMPOUNDS WITH ORGANOTIN COMPOUNDS [J].
WARDELL, JL ;
AHMED, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 78 (03) :395-404
[40]   STANNYLATION-IODINATION REACTION ON PYRIDINE NUCLEI - A FACILE METHOD FOR SYNTHESIS OF IODOPYRIDINES AND IODOQUINOLINES [J].
YAMAMOTO, Y ;
YANAGI, A .
HETEROCYCLES, 1981, 16 (07) :1161-1164