Haloamidation of alkynes and related reactions using zirconacycles and isocyanates

被引：39

作者：

Li, YZ

Matsumura, H

Yamanaka, M

Takahashi, T ^{[1
]}

机构：

[1] Hokkaido Univ, Ctr Catalysis Res, Kita Ku, Sapporo, Hokkaido 0600811, Japan

[2] Hokkaido Univ, Grad Sch Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600811, Japan

[3] Sci & Technol Corp, CREST, JST, Sapporo, Hokkaido 0600811, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 06期

关键词：

zirconacyclopentene; zirconacyclopentadiene; zirconacyclopentane; haloamidation; isocyanate; isocyanurate; trimerization of isocyanate;

D O I：

10.1016/j.tet.2003.08.078

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Zirconacyclopentenes reacted with isocyanates to give aza- or oxazirconacycles which were conveniently coverted into the corresponding haloamidation products of alkynes after halogenation. 1,4-Bistrimethylsilyl substituted zirconacyclopentadiene afforded a low yield of iodoamidation product, whereas zirconium-alkyne complexes stabilized with phosphine gave the iodoamidation products in moderate yields. On the other hand, zirconacyclopentanes reacted with isocyanates to give trimerization products of isocyanate, isocyanurates. (C) 2003 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1393 / 1400

页数：8

相关论文

共 34 条

[1] ORGANOMETALLIC REACTIONS .3. TRIMERISATION OF ISOCYANATES BY ORGANOTIN ALKOXIDES AND OXIDES [J].

BLOODWOR.AJ ;

DAVIES, AG .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (DEC) :6858-&

[2]

Grotjahn D. B, 1995, COMPREHENSIVE ORGANO, V12, P741

[3] NEW REACTIONS OF PHENYL ISOCYANATE AND ETHYL ALCOHOL [J].

KOGON, IC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (19) :4911-4914

[4] Cross coupling conjugate addition reaction of zirconacyclopentadienes with 3-iodopropenoates [J].

Kotora, M ;

Xi, CJ ;

Takahashi, T .

TETRAHEDRON LETTERS, 1998, 39 (24) :4321-4324

[5] Alkynylzirconation of alkynes and application to one-pot bisalkynylation of alkynes [J].

Liu, YH ;

Zhong, ZQ ;

Nakajima, K ;

Takahashi, T .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7451-7456

[6] CYCLOTRIMERIZATION OF ARYL ISOCYANATES CATALYZED BY ALKOXYALLENES THROUGH ZWITTERIONIC MECHANISM [J].

MIZUYA, J ;

YOKOZAWA, T ;

ENDO, T .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1991, 29 (11) :1545-1548

[7] SYNTHESIS OF NOVEL AROMATIC ISOCYANURATES BY THE FLUORIDE-CATALYZED SELECTIVE TRIMERIZATION OF ISOCYANATES [J].

NAMBU, Y ;

ENDO, T .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) :1932-1934

[8] METAL-PROMOTED CYCLIZATION .11. REACTION OF ZIRCONOCENE DICHLORIDE WITH ALKYLLITHIUMS OR ALKYL GRIGNARD-REAGENTS AS A CONVENIENT METHOD FOR GENERATING A ZIRCONOCENE EQUIVALANT AND ITS USE IN ZIRCONIUM-PROMOTED CYCLIZATION OF ALKENES, ALKYNES, DIENES, ENYNES, AND DIYNES [J].

NEGISHI, E ;

CEDERBAUM, FE ;

TAKAHASHI, T .

TETRAHEDRON LETTERS, 1986, 27 (25) :2829-2832

[9] METAL-PROMOTED CYCLIZATION .19. NOVEL BICYCLIZATION OF ENYNES AND DIYNES PROMOTED BY ZIRCONOCENE DERIVATIVES AND CONVERSION OF ZIRCONABICYCLES INTO BICYCLIC ENONES VIA CARBONYLATION [J].

NEGISHI, E ;

HOLMES, SJ ;

TOUR, JM ;

MILLER, JA ;

CEDERBAUM, FE ;

SWANSON, DR ;

TAKAHASHI, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3336-3346

[10]

NOLTES JG, 1967, J ORGANOMET CHEM, V7, P6

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