Synthesis of coumarins via palladium-catalyzed carbonylative annulation of internal alkynes by o-iodophenols

被引:133
作者
Kadnikov, DV [1 ]
Larock, RC [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
关键词
D O I
10.1021/ol0065569
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A variety of substituted coumarins have been prepared in good yields by the palladium-catalyzed coupling of o-iodophenols with internal alkynes and 1 atm of carbon monoxide, Unlike most of the previous work on the palladium catalyzed carbonylation of alkynes, the insertion of the internal alkyne occurs in preference to the insertion of CO.
引用
收藏
页码:3643 / 3646
页数:4
相关论文
共 29 条
[1]   PALLADIUM-CATALYZED SYNTHESIS OF COUMARIN [J].
AN, ZW ;
CATELLANI, M ;
CHIUSOLI, GP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 371 (03) :C51-C52
[2]  
[Anonymous], 2 P INT SOC COUM INV
[3]  
AWASTHI AK, 1986, SYNTHESIS-STUTTGART, P1061
[4]   A NEW PALLADIUM-CATALYZED SYNTHESIS OF 3,4-DISUBSTITUTED COUMARINS FROM 3-ALKENOATES OF ORTHO-IODOPHENOL, PHENYLACETYLENE AND CARBON-MONOXIDE [J].
CATELLANI, M ;
CHIUSOLI, GP ;
FAGNOLA, MC ;
SOLARI, G .
TETRAHEDRON LETTERS, 1994, 35 (32) :5923-5926
[5]   INTRAMOLECULAR CYCLIZATION OF ORTHO-IODOPHENYL 3-BUTENOATE TO 4-METHYLCOUMARIN - CATALYSIS BY PALLADIUM COMPLEXES [J].
CATELLANI, M ;
CHIUSOLI, GP ;
FAGNOLA, MC ;
SOLARI, G .
TETRAHEDRON LETTERS, 1994, 35 (32) :5919-5922
[6]   ACYLPALLADATION OF INTERNAL ALKYNES AND PALLADIUM-CATALYZED CARBONYLATION OF (Z)-BETA-IODOENONES AND RELATED DERIVATIVES PRODUCING GAMMA-LACTONES AND GAMMA-LACTAMS [J].
COPERET, C ;
SUGIHARA, T ;
WU, GZ ;
SHIMOYAMA, I ;
NEGISHI, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) :3422-3431
[7]   CARBON-MONOXIDE AS A ONE-CARBON COMPONENT IN PALLADIUM-CATALYZED CYCLOADDITION REACTIONS [J].
GRIGG, R ;
KHALIL, H ;
LEVETT, P ;
VIRICA, J ;
SRIDHARAN, V .
TETRAHEDRON LETTERS, 1994, 35 (19) :3197-3200
[8]  
Johnson J.R., 1942, Organic Reactions, Org. React., V1, P210, DOI DOI 10.1002/0471264180.OR001.08
[9]   Synthesis of polycyclic aromatic hydrocarbons by the Pd-catalyzed annulation of alkynes [J].
Larock, RC ;
Doty, MJ ;
Tian, QP ;
Zenner, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7536-7537
[10]   SYNTHESIS OF AROMATIC HETEROCYCLES VIA PALLADIUM-CATALYZED ANNULATION OF INTERNAL ALKYNES [J].
LAROCK, RC ;
YUM, EK ;
DOTY, MJ ;
SHAM, KKC .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) :3270-3271