Rhodium-catalyzed one-pot hydroformylation-cyclization of allylbenzene derivatives: Simple and efficient route to 5,6-dihydronaphthalenes

被引：9

作者：

Alhaffar, Mouheddin ^{[1
]}

Suleiman, Rami ^{[1
]}

El Ali, Bassam ^{[1
]}

机构：

[1] King Fahd Univ Petr & Minerals, Dept Chem, Dhahran 31261, Saudi Arabia

来源：

CATALYSIS COMMUNICATIONS | 2010年 / 11卷 / 08期

关键词：

Allylbenzene; Eugenol; Hydroformylation; Cyclization; Dihydronaphthalenes; Rhodium; Phosphite; Ultranox626; RING; DIHYDRONAPHTHALENES; 1,2-DIHYDRONAPHTHALENES; ALKENES;

D O I：

10.1016/j.catcom.2010.02.014

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The one-pot hydroformylation-cyclization of allylbenzene derivatives by the catalyst system Rh(CO)(2)a-cac/ultranox626/CO/H(2)/CH(2)Cl(2) led chemoselectively to 5,6-dihydronaphthalene derivatives 5a-d in good yields. The addition of a catalytic amount of H(3)PO(4) enhanced in situ the cyclization process via the nucleophilic attack on the carbonyl group of the linear aldehyde, and finally the elimination of alcohol. The type of substitution on phenyl group of the allylbenzene is of great importance in enhancing the cyclization process. (C) 2010 Elsevier B.V. All rights reserved.

引用

页码：778 / 782

页数：5

共 21 条

[1] Functionalized 1,2-dihydronaphthalenes from the Cu(OTf)2-catalyzed [4+2] cycloaddition of o-alkynyl(oxo)benzenes with alkenes [J].

Asao, N ;

Kasahara, T ;

Yamamoto, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (30) :3504-3506

[2] Rhodium-diphosphite catalysed hydroformylation of allylbenzene and propenylbenzene derivatives [J].

Axet, M. Rosa ;

Castillon, Sergio ;

Claver, Carmen .

INORGANICA CHIMICA ACTA, 2006, 359 (09) :2973-2979

[3] Ru(II)- and Pt(II)-catalyzed cycloisomerization of ω-aryl-1-alkynes.: Generation of carbocationic species from alkynes and transition metal halides and its interception by an aromatic ring [J].

Chatani, N ;

Inoue, H ;

Ikeda, T ;

Murai, S .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :4913-4918

[4] Potential antidepressants displayed combined α2-adrenoceptor antagonist and monoamine uptake inhibitor properties [J].

Cordi, AA ;

Berque-Bestel, I ;

Persigand, T ;

Lacoste, JM ;

Newman-Tancredi, A ;

Audinot, V ;

Millan, MJ .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (05) :787-805

[5] Rhodium-catalyzed hydroformylation of allylbenzenes and propenylbenzenes: effect of phosphine and diphosphine ligands on chemo- and regioselectivity [J].

da Silva, AC ;

de Oliveira, KCB ;

Gusevskaya, EV ;

dos Santos, EN .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 179 (1-2) :133-141

[6] Acid-catalyzed cyclization of 2,3-dibenzylidenesuccinates:: Synthesis of lignans (±)-cagayanin and (±)-galbulin [J].

Datta, PK ;

Yau, C ;

Hooper, TS ;

Yvon, BL ;

Charlton, JL .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8606-8611

[7]

GASLINI F, 1964, J ORG CHEM, P1177

[8] Synthesis of hindered 1-arylnaphthalene derivatives via ring expansion of benzocyclobutenones [J].

Hamura, T ;

Miyamoto, M ;

Matsumoto, T ;

Suzuki, K .

ORGANIC LETTERS, 2002, 4 (02) :229-232

[9] Stereochemical anomaly in the thermal conversion of 7,8-dioxy-7-alkenylbenzocyclobutenes to dihydronaphthalenes [J].

Hamura, T ;

Miyamoto, M ;

Imura, K ;

Matsumoto, T ;

Suzuki, K .

ORGANIC LETTERS, 2002, 4 (10) :1675-1678

[10] Intramolecular electrophilic aromatic substitution reactions with methyl vinyl ethers for the synthesis of dihydronaphthalenes [J].

Harrowven, DC ;

Tyte, MJ .

TETRAHEDRON LETTERS, 2002, 43 (34) :5971-5972

← 1 2 3 →