Cobalt-catalyzed allylzincations of internal alkynes

被引：28

作者：

Yasui, Hiroto ^{[1
]}

Nishikawa, Toshihiro ^{[1
]}

Yorimitsu, Hideki ^{[1
]}

Oshima, Koichiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2006年 / 79卷 / 08期

关键词：

D O I：

10.1246/bcsj.79.1271

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cobalt salts such as cobalt(II) chloride catalyze allylzincation reactions of 1-aryl-1-alkynes. The allylzincations proceed in a syn fashion to form 2-allyl-1-aryl-1-alkenylzinc species. Other internal alkynes such as 6-dodecyne or 2-nonyn-1-ol are much less reactive than 1-aryl-1-alkynes.

引用

页码：1271 / 1274

页数：4

共 24 条

[1] GAMMA-FUNCTIONAL VINYLIC GRIGNARD-REAGENTS .1. REACTIVITY OF ORGANOMAGNESIUM COMPOUNDS WITH ALPHA-ACETYLIC ALCOHOLS IN THE PRESENCE OF CUPROUS HALIDES [J].

DUBOUDIN, JG ;

JOUSSEAUME, B .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 168 (01) :1-11

[2] GAMMA-FUNCTIONAL VINYL GRIGNARD-REAGENTS .2. IODOLYSIS, ALKYLATION AND ARYLATION OF IODO-ALCOHOLS [J].

DUBOUDIN, JG ;

JOUSSEAUME, B ;

BONAKDAR, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 168 (02) :227-232

[3]

Knochel P., 1995, COMPREHENSIVE ORGA 2, V11, P159

[4]

Knochel P., 1991, COMPREHENSIVE ORGANI, V4, P865

[5]

Marek I, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P271

[6] Cobalt-catalyzed allylic substitution reaction of allylic ethers with phenyl and trimethylsilylmethyl Grignard reagents [J].

Mizutani, K ;

Yorimitsu, H ;

Oshima, K .

CHEMISTRY LETTERS, 2004, 33 (07) :832-833

[7] SELECTIVE CARBON CARBON BOND FORMATION VIA TRANSITION-METAL CATALYSIS .37. CONTROLLED CARBOMETALATION .16. NOVEL SYNTHESES OF ALPHA,BETA-UNSATURATED CYCLOPENTENONES VIA ALLYLZINCATION OF ALKYNES [J].

NEGISHI, E ;

MILLER, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) :6761-6763

[8] BIMETALLIC CATALYTIC-SYSTEMS CONTAINING TI, ZR, NI, AND PD - THEIR APPLICATIONS TO SELECTIVE ORGANIC SYNTHESES [J].

NEGISHI, E .

PURE AND APPLIED CHEMISTRY, 1981, 53 (12) :2333-2356

[9]

NEGISHI E, 1996, CHEM REV, V96, P417

[10] Cobalt-catalyzed regio- and stereoselective allylzincation of 1-phenyl-1-alkynes [J].

Nishikawa, T ;

Yorimitsu, H ;

Oshima, K .

SYNLETT, 2004, (09) :1573-1574

← 1 2 3 →