Palladium-catalyzed esterification-hydroarylation reactions of 2-alkynylbenzaldehydes with aryl iodides in methanol

被引：53
作者：
Wei, LL
Wei, LM
Pan, WB
Wu, MJ [1 ]
机构：
[1] Kaohsiung Med Univ, Fac Med & Appl Chem, Kaohsiung 807, Taiwan
[2] Fooyin Univ, Kaohsiung 831, Taiwan
[3] Kaohsiung Med Univ, Grad Inst Pharmaceut Sci, Kaohsiung 807, Taiwan
来源：
SYNLETT | 2004年 / 09期
关键词：
palladium; coupling; esterification-hydroarylation; 2-alkynylbenzaldehydes;
D O I：
10.1055/s-2004-829056
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of 2-alkynylbenzaldehydes with aryl iodides in the presence of Pd(PPh3)(4) and K2CO3 in refluxing methanol for 24 hours gave the dehydrogenation-addition products, methyl 2(2,2-disubstituted-vinyl)benzoates in modest yields; together with the cyclization products, 3-methoxy-1-inonosubstituted-methylene-3-hydroisobenzofurans in 3-18% yields.
引用
收藏
页码：1497 / 1502
页数：6
相关论文
共 32 条
[1]  
ARCADI A, 1992, TETRAHEDRON LETT, V33, P3915
[2]   PALLADIUM-CATALYZED REACTION OF VINYL TRIFLATES AND VINYL ARYL HALIDES WITH 4-ALKYNOIC ACIDS - REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (E)-DELTA-VINYL ARYL-GAMMA-METHYLENE-GAMMA-BUTYROLACTONES [J].
ARCADI, A ;
BURINI, A ;
CACCHI, S ;
DELMASTRO, M ;
MARINELLI, F ;
PIETRONI, BR .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :976-982
[3]   Palladium-catalyzed reaction of o-ethynylphenols, o-((trimethylsilyl)ethynyl)phenyl acetates, and o-alkynylphenols with unsaturated triflates or halides: A route to 2-substituted-, 2,3-disubstituted-, and 2-substituted-3-acylbenzo[b]furans [J].
Arcadi, A ;
Cacchi, S ;
DelRosario, M ;
Fabrizi, G ;
Marinelli, F .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9280-9288
[4]  
ARCADI A, 1986, SYNTHESIS-STUTTGART, P749
[5]   Pd(II) acts simultaneously as a Lewis acid and as a transition-metal catalyst: Synthesis of cyclic alkenyl ethers from acetylenic aldehydes [J].
Asao, N ;
Nogami, T ;
Takahashi, K ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :764-765
[6]   TOTAL SYNTHESIS OF THE TRIQUINANE MARINE SESQUITERPENE (PLUS-OR-MINUS)DELTA(9(12)) CAPNELLENE USING A PALLADIUM-CATALYZED BIS-CYCLIZATION STEP [J].
BALME, G ;
BOUYSSI, D .
TETRAHEDRON, 1994, 50 (02) :403-414
[7]   Nucleophilic transition metal based cyclization of allenes [J].
Bates, RW ;
Satcharoen, V .
CHEMICAL SOCIETY REVIEWS, 2002, 31 (01) :12-21
[8]   SYNTHESIS OF ETHYNYLIDENE CYCLOPENTANES BY A CYCLIZATION CATALYZED BY THE SIMULTANEOUS PRESENCE OF PALLADIUM(O) AND COPPER(I) [J].
BOUYSSI, D ;
BALME, G ;
GORE, J .
TETRAHEDRON LETTERS, 1991, 32 (45) :6541-6544
[9]   PALLADIUM-CATALYZED SYNTHESIS OF NEW UNSATURATED EXO-ENOL LACTONES WITH POTENTIAL BIOLOGICAL-ACTIVITY [J].
BOUYSSI, D ;
GORE, J ;
BALME, G ;
LOUIS, D ;
WALLACH, J .
TETRAHEDRON LETTERS, 1993, 34 (19) :3129-3130
[10]   A steric control of regioselectivity in palladium-catalyzed cyclizations of alkenes bearing arylbromides and nucleophiles [J].
Bruyere, D ;
Gaignard, G ;
Bouyssi, D ;
Balme, G ;
Lancelin, JM .
TETRAHEDRON LETTERS, 1997, 38 (05) :827-830
1234