Nickel-catalyzed carboannulation reaction of o-bromobenzyl zinc bromide with unsaturated compounds

被引：32

作者：

Deng, Ruixue ^{[1
]}

Sun, Liangdong ^{[1
]}

Li, Zhi ^{[1
]}

机构：

[1] Tianjin Univ, Sch Sci, Dept Chem, Tianjin 300072, Peoples R China

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 25期

关键词：

D O I：

10.1021/ol702167t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of indenes have been prepared in good yields by treating o-bromobenzyl zinc bromide 1 with various terminal and internal alkynes in the presence of a nickel catalyst. The nickel-catalyzed carboannulation reaction was successfully extended to the synthesis of indane derivatives by reaction of 1 with acrylates and styrene.

引用

页码：5207 / 5210

页数：4

共 45 条

[1] Effect of the nature of metallocene complexes of group IV metals on their performance in catalytic ethylene and propylene polymerization [J].

Alt, HG ;

Köppl, A .

CHEMICAL REVIEWS, 2000, 100 (04) :1205-1221

[2] SYNTHESIS AND SINGLE-CRYSTAL X-RAY STUDY OF THE MONONUCLEAR ETA-2-BENZYNE (DEHYDROBENZENE) NICKEL(0) COMPLEX NI(ETA-2-C6H4)((C6H11)2PCH2CH2P(C6H11)2) - INSERTION REACTIONS WITH SIMPLE MOLECULES AND X-RAY CRYSTAL-STRUCTURE OF THE NICKELAINDAN COMPLEX NI(CH2CH2C6H4-O)((C6H11)2PCH2CH2P(C6H11)2) [J].

BENNETT, MA ;

HAMBLEY, TW ;

ROBERTS, NK ;

ROBERTSON, GB .

ORGANOMETALLICS, 1985, 4 (11) :1992-2000

[3] PREPARATION AND REACTIONS OF FUNCTIONALIZED BENZYLIC ORGANOMETALLICS OF ZINC AND COPPER [J].

BERK, SC ;

YEH, MCP ;

JEONG, N ;

KNOCHEL, P .

ORGANOMETALLICS, 1990, 9 (12) :3053-3064

[4] GENERAL-APPROACH TO HIGHLY FUNCTIONALIZED BENZYLIC ORGANOMETALLICS OF ZINC AND COPPER [J].

BERK, SC ;

KNOCHEL, P ;

YEH, MCP .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5789-5791

[5] Indenyl complexes of Group 8 metals [J].

Cadierno, V ;

Diez, J ;

Gamasa, MP ;

Gimeno, J ;

Lastra, E .

COORDINATION CHEMISTRY REVIEWS, 1999, 193-5 :147-205

[6] STEPWISE REACTION OF CS2 WITH THE NICKELACYCLOPENTENE COMPLEXES (R3P)2NI(CH2CME2-O-C6H4) - INFLUENCE OF THE ANCILLARY PHOSPHINE-LIGANDS [J].

CAMPORA, J ;

CARMONA, E ;

GUTIERREZPUEBLA, E ;

POVEDA, ML ;

RUIZ, C .

ORGANOMETALLICS, 1988, 7 (12) :2577-2579

[7] REACTIONS OF THE BENZONICKELACYCLOPENTENE COMPLEX (ME3P)2NI(CH2CME2-O-C6H4) WITH ALKYNES - SYNTHESIS OF 1,2-DIHYDRONAPHTHALENES [J].

CAMPORA, J ;

LLEBARIA, A ;

MORETO, JM ;

POVEDA, ML ;

CARMONA, E .

ORGANOMETALLICS, 1993, 12 (10) :4032-4038

[8] CONSECUTIVE INSERTION REACTIONS OF UNSATURATED MOLECULES INTO THE NI-C BONDS OF THE NICKELACYCLE - (ME3P)2NI(CH2CME2-O-C6H4) - FORMATION OF HETEROCYCLES DERIVED FROM 7-MEMBERED CYCLIC ACID ANHYDRIDES [J].

CAMPORA, J ;

GUTIERREZ, E ;

MONGE, A ;

PALMA, P ;

POVEDA, ML ;

RUIZ, C ;

CARMONA, E .

ORGANOMETALLICS, 1994, 13 (05) :1728-1745

[9] SYNTHESIS AND X-RAY STRUCTURE OF THE NICKELABENZOCYCLOPENTENE COMPLEX (ME3P)2NI(CH2CME2-ORTHO-C6H4) - REACTIVITY TOWARD SIMPLE, UNSATURATED MOLECULES AND THE CRYSTAL AND MOLECULAR-STRUCTURE OF THE CYCLIC CARBOXYLATE (ME3P)2NI(CH2CME2-ORTHO-C6H4C(O)O) [J].

CARMONA, E ;

GUTIERREZPUEBLA, E ;

MARIN, JM ;

MONGE, A ;

PANEQUE, M ;

POVEDA, ML ;

RUIZ, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :2883-2891

[10] SYNTHESIS OF (ME3P)2NI(CH2CME2-ORTHO-C6H4) AND ITS REACTIVITY TOWARD CO2, CO, AND CH2O - 1ST OBSERVATION OF A CARBONYL-CARBONATE OXIDATIVE CONPROPORTIONATION MEDIATED BY A TRANSITION-METAL COMPLEX [J].

CARMONA, E ;

PALMA, P ;

PANEQUE, M ;

POVEDA, ML ;

GUTIERREZPUEBLA, E ;

MONGE, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6424-6425

← 1 2 3 4 5 →