Nickel-catalyzed intermolecular alkyne insertion into cyclobutanones

被引：161

作者：

Murakami, M ^{[1
]}

Ashida, S ^{[1
]}

Matsuda, T ^{[1
]}

机构：

[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 19期

关键词：

D O I：

10.1021/ja050674f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclobutanones reacted with alkynes in the presence of nickel(0) catalysts to produce cyclohexenones. Oxidative cyclization of the carbonyl group of the cyclobutanone and the alkyne with the nickel(0) was followed by β-carbon elimination from the resulting oxanickelacyclopentene and subsequent reductive elimination. This reaction achieves a formal alkyne insertion between the carbonyl carbon and the α-carbon, providing a six-membered carbocyclic skeleton. Copyright © 2005 American Chemical Society.

引用

页码：6932 / 6933

页数：2

共 24 条

[1] THE ORGANOMETALLIC CHEMISTRY OF ALKANES [J].

CRABTREE, RH .

CHEMICAL REVIEWS, 1985, 85 (04) :245-269

[2] Cobalt-mediated two-carbon ring expansion of five-membered rings. Electrophilic carbon-carbon bond activation in the synthesis of seven-membered rings [J].

Dzwiniel, TL ;

Stryker, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9184-9185

[3] NICKEL(0)-CATALYZED SYNTHESIS OF SUBSTITUTED PHENOLS FROM CYCLOBUTENONES AND ALKYNES [J].

HUFFMAN, MA ;

LIEBESKIND, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) :2771-2772

[4] INSERTION OF (ETA-5-INDENYL)COBALT(I) INTO CYCLOBUTENONES - THE 1ST SYNTHESIS OF PHENOLS FROM ISOLATED VINYLKETENE COMPLEXES [J].

HUFFMAN, MA ;

LIEBESKIND, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8617-8618

[5] Diverse pathways in ring-opening Ziegler polymerization of an annulated methylenecyclopropane. A new single-site chain transfer mechanism [J].

Jensen, TR ;

Marks, TJ .

MACROMOLECULES, 2003, 36 (06) :1775-1778

[6] Transition metal-catalyzed carbon-carbon bond activation [J].

Jun, CH .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) :610-618

[7] Ru- and Rh-catalyzed C-C bond cleavage of cyclobutenones: Reconstructive and selective synthesis of 2-pyranones, cyclopentenes, and cyclohexenones [J].

Kondo, T ;

Taguchi, Y ;

Kaneko, Y ;

Niimi, M ;

Mitsudo, TA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (40) :5369-5372

[8] Ligand-dependent scope and divergent mechanistic behavior in nickel-catalyzed reductive couplings of aldehydes and alkynes [J].

Mahandru, GM ;

Liu, G ;

Montgomery, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) :3698-3699

[9] Eight-membered ring formation via olefin insertion into a carbon-carbon single bond [J].

Matsuda, T ;

Fujimoto, A ;

Ishibashi, M ;

Murakami, M .

CHEMISTRY LETTERS, 2004, 33 (07) :876-877

[10] Rhodium-catalyzed addition/ring-opening reaction of arylboronic acids with cyclobutanones [J].

Matsuda, T ;

Makino, M ;

Murakami, M .

ORGANIC LETTERS, 2004, 6 (08) :1257-1259

← 1 2 3 →