Mercuric triflate-(TMU)3-catalyzed cyclization of ω-arylalkyne leading to dihydronaphthalenes

被引：101

作者：

Nishizawa, M ^{[1
]}

Takao, H ^{[1
]}

Yadav, VK ^{[1
]}

Imagawa, H ^{[1
]}

Sugihara, T ^{[1
]}

机构：

[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Tokushima 7708514, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 24期

关键词：

D O I：

10.1021/ol035622e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient arylyne cyclization catalyzed by the Hg(OTf)(2)-(TMU)(3) complex has been developed. The reaction was carried out at ambient temperature in acetonitrile, and the catalytic cycle reaches up to 1000 turnovers.

引用

页码：4563 / 4565

页数：3

共 30 条

[1] Lewis acid catalyzed stereoselective carbosilylation.: Intramolecular trans-vinylsilylation and trans-arylsilylation of unactivated alkynes [J].

Asao, N ;

Shimada, T ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10899-10902

[2] ACID CATALYSIS OF CLAISEN REARRANGEMENT .2. FORMATION OF BENZOFUROBENZOPYRAN AND BENZOFURO[3,2-B]BENZOFURAN SKELETONS FROM 1,4-BIS(ARYLOXY)-2-BUTYNES [J].

BATES, DK ;

JONES, MC .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20) :3856-3861

[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] Flexible synthesis of phenanthrenes by PtCl2-catalyzed cycloisomerization reaction [J].

Fürstner, A ;

Mamane, V .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) :6264-6267

[5]

Imagawa H, 1998, CHEM PHARM BULL, V46, P1341

[6] Cycloisomerization of ω-aryl-1-alkynes:: GaCl3 as a highly electrophilic catalyst for alkyne activation [J].

Inoue, H ;

Chatani, N ;

Murai, S .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1414-1417

[7] New method for preparation of coumarins and quinolinones via Pd-catalyzed intramolecular hydroarylation of C-C triple bonds [J].

Jia, C ;

Piao, D ;

Kitamura, T ;

Fujiwara, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22) :7516-7522

[8] SILVER ION CATALYZED REARRANGEMENT OF PROPARGYLPHENYLETHERS [J].

KOCHPOME.U ;

JURGENHA.H ;

SCHMID, H .

HELVETICA CHIMICA ACTA, 1973, 56 (08) :2981-3004

[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] MERCURY IN ORGANIC-CHEMISTRY .26. SYNTHESIS OF HETEROCYCLES VIA INTRAMOLECULAR SOLVOMERCURATION OF ARYL ACETYLENES [J].

LAROCK, RC ;

HARRISON, LW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (15) :4218-4227

← 1 2 3 →