Transition metal-catalyzed cyclization of 2-allylphenol to 2,3-dihydro-2-methylbenzofuran without β-elimination

被引：36

作者：

Hori, K ^{[1
]}

Kitagawa, H ^{[1
]}

Miyoshi, A ^{[1
]}

Ohta, T ^{[1
]}

Furukawa, I ^{[1
]}

机构：

[1] Doshisha Univ, Fac Engn, Dept Mol Sci & Technol, Kyoto 6100394, Japan

来源：

CHEMISTRY LETTERS | 1998年 / 11期

关键词：

D O I：

10.1246/cl.1998.1083

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The intramolecular nucleophilic addition of 2-allylphenol was catalyzed by RuCl3. nH(2)O/AgOTf-PPh3-Cu(OTf)(2) to afford 2,3-dihydro-2-methylbenzofuran in good yield, while 2-(3-butenyl)phenol was converted to 3,4-dihydro-2(2H) -methylbenzopyran.

引用

页码：1083 / 1084

页数：2

共 46 条

[1]

Barton D., 1979, COMPREHENSIVE ORGANI, V1

[2] REACTION OF (DPPE)PT(CH3)(OCH3) WITH TETRAFLUOROETHYLENE - SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF (DPPE)PT(CH3)(CF2CF2OCH3) [J].

BRYNDZA, HE ;

CALABRESE, JC ;

WREFORD, SS .

ORGANOMETALLICS, 1984, 3 (10) :1603-1604

[3]

Collman J.P., 1987, PRINCIPLES APPL ORGA

[4]

CORNIS B, 1996, APPL HOMOGENEOUS CAT, V2

[5]

CORNIS B, 1996, APPL HOMOGENEOUS CAT, V1

[6] A MODEL FOR OLEFIN HYDRATION - INTRAMOLECULAR NUCLEOPHILIC-ADDITION OF PHENOLATE OXYGEN TO THE UNACTIVATED DOUBLE-BOND [J].

EVANS, CM ;

KIRBY, AJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (07) :1259-1267

[7]

FITTON AO, 1968, PRACTICAL HETEROCYCL, P16

[8] UBER DIE PHOTOCHEMISCHE CYCLISIERUNG VON 2-ALLYLPHENOLEN [J].

FRATER, G ;

SCHMID, H .

HELVETICA CHIMICA ACTA, 1967, 50 (01) :255-&

[9] ISOMERIZATION OF ALLYL PHENYL ETHERS AND ALLYLPHENOLS WITH TRANSITION-METAL CATALYSTS [J].

GOLBORN, P ;

SCHEINMANN, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (23) :2870-2875

[10] PALLADIUM-CATALYZED REACTIONS IN THE SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED INDOLES - APPROACHES TO ERGOT ALKALOIDS [J].

HARRINGTON, PJ ;

HEGEDUS, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (15) :2657-2662

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