Efficient coupling reactions of lithium alkynyl(triisopropoxy)borates with aryl halides: application to the antifungal terbinafine synthesis

被引：37

作者：

Oh, CH ^{[1
]}

Jung, SH ^{[1
]}

机构：

[1] Hanyang Univ, Dept Chem, Sungdong Gu, Seoul 133791, South Korea

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 44期

关键词：

palladium; alkyne; antifungal agent; terbinafine;

D O I：

10.1016/S0040-4039(00)01543-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thermally stable lithium alkynyl(triisopropoxy)borates were reacted with several aryl halides in the presence of palladium catalysts to give the corresponding cross-coupling products in excellent yields. The present methodology has been successfully applied to the antifungal terbinafine synthesis. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：8513 / 8516

页数：4

共 17 条

[1] A two-step synthesis of terbinafine [J].

Alami, M ;

Ferri, F ;

Gaslain, Y .

TETRAHEDRON LETTERS, 1996, 37 (01) :57-58

[2]

[Anonymous], 1999, J CHEM EDUC

[3] A SIMPLE, GENERAL-SYNTHESIS OF 1-ALKYNYLDIISOPROPOXYBORANES [J].

BROWN, HC ;

BHAT, NG ;

SREBNIK, M .

TETRAHEDRON LETTERS, 1988, 29 (22) :2631-2634

[4] SYNTHESIS OF ARYL-SUBSTITUTED AND VINYL-SUBSTITUTED ACETYLENE DERIVATIVES BY USE OF NICKEL AND PALLADIUM COMPLEXES [J].

CASSAR, L .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :253-257

[5] PALLADIUM CATALYZED SYNTHESIS OF ARYL, HETEROCYCLIC AND VINYLIC ACETYLENE DERIVATIVES [J].

DIECK, HA ;

HECK, FR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :259-263

[6]

Heck R.F., 1985, PALLADIUM REAGENTS O

[7] PALLADIUM-CATALYZED REACTIONS OF ORGANIC HALIDES WITH OLEFINS [J].

HECK, RF .

ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (04) :146-151

[8]

KIM G, 1995, B KOR CHEM SOC, V16, P1002

[9] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].

MIYAURA, N ;

SUZUKI, A .

CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483

[10] CONJUGATE ADDITION-ELIMINATION IN REACTION OF B-1-ALKYNYL-9-BORABICYCLO[3.3.1]NONANES WITH 4-METHOXY-3-BUTEN-2-ONE AND RELATED DERIVATIVES - CONVENIENT NEW ROUTE TO CONJUGATED ENYNONES [J].

MOLANDER, GA ;

BROWN, HC .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (18) :3106-3108

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