Palladium-catalyzed tandem Heck and aldol reactions between 2-bromobenzaldehydes and functionalized alkenes leading to naphthalenes

被引:33
作者
Cho, CS [1 ]
Lim, DK
Zhang, JQ
Kim, TJ
Shim, SC
机构
[1] Kyungpook Natl Univ, Coll Engn, Dept Appl Chem, Taegu 702701, South Korea
[2] Kyungpook Natl Univ, Ind Technol Res Inst, Taegu 702701, South Korea
关键词
2-bromobenzaldehydes; functionalized alkenes; Heck-aldol reaction; naphthalenes palladium catalyst;
D O I
10.1016/j.tetlet.2004.05.112
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Bromobenzaldehydes react with an array of suitably functionalized alkenes in the presence of a catalytic amount of a palladium catalyst together with a base to afford the corresponding naphthalenes in moderate to good yields. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5653 / 5656
页数:4
相关论文
共 17 条
[1]   Palladium-catalyzed cross-coupling of 3-iodobut-3-enoic acid with organometallic reagents.: Synthesis of 3-substituted but-3-enoic acids [J].
Abarbri, M ;
Parrain, JL ;
Kitamura, M ;
Noyori, R ;
Duchêne, A .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22) :7475-7478
[2]  
BENAYED T, 1995, SYNTHETIC COMMUN, V25, P3813
[3]  
Cho CS, 2002, J CHEM RES-S, P550
[4]   Facile palladium-catalysed synthesis of 1-aryl-1H-indazoles from 2-bromobenzaldehydes and arylhydrazines [J].
Cho, CS ;
Lim, DK ;
Heo, NH ;
Kim, TJ ;
Shim, SC .
CHEMICAL COMMUNICATIONS, 2004, (01) :104-105
[5]   Synthesis of isoindolinones via carbonylative cyclisation of 2-(2-bromophenyl)-2-oxazolines by a bimetallic palladium-nickel catalyst system [J].
Cho, CS ;
Lee, JW ;
Lee, DY ;
Shim, SC ;
Kim, TJ .
CHEMICAL COMMUNICATIONS, 1996, (18) :2115-2116
[6]   Synthesis of isoindolin-1-ones via palladium-catalyzed intermolecular coupling and heteroannulation between 2-iodobenzoyl chloride and imines [J].
Cho, CS ;
Shim, HS ;
Choi, HJ ;
Kim, TJ ;
Shim, SC ;
Kim, MC .
TETRAHEDRON LETTERS, 2000, 41 (20) :3891-3893
[7]   Annulated ring-systems by Domino-Heck-Aldol-condensation and Domino-Heck-Michael-addition processes [J].
Dyker, G ;
Grundt, P .
TETRAHEDRON LETTERS, 1996, 37 (05) :619-622
[8]   Palladium-catalyzed highly chemo- and regioselective formal [2+2+2] sequential cycloaddition of alkynes: A renaissance of the well known trimerization reaction? [J].
Gevorgyan, V ;
Radhakrishnan, U ;
Takeda, A ;
Rubina, M ;
Rubin, M ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2835-2841
[9]   Synthesis of indenols and indanones via catalytic cyclic vinylpalladation of aromatic aldehydes [J].
Gevorgyan, V ;
Quan, LG ;
Yamamoto, Y .
TETRAHEDRON LETTERS, 1999, 40 (21) :4089-4092
[10]   Heterocycles via Pd catalysed molecular queuing processes. Relay switches and the maximisation of molecular complexity [J].
Grigg, R ;
Sridharan, V .
PURE AND APPLIED CHEMISTRY, 1998, 70 (05) :1047-1057