New efficient nickel-catalyzed cross-coupling reaction between two Csp3 centers

被引：139

作者：

Giovannini, R

Stüdemann, T

Devasagayaraj, A

Dussin, G

Knochel, P

机构：

[1] Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany

[2] Univ Munich, Inst Organ Chem, D-81377 Munich, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 10期

关键词：

D O I：

10.1021/jo982317b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The presence of a remote unsaturation (double bond, carbonyl group, cyano group) in an alkyl halide facilitates its cross-coupling reaction with various diorganozincs in the presence of Ni(acac)(2) (7.5-10 mol % in THF/NMP mixtures). These results were used to develop a new general cross-coupling reaction between functionalized diorganozincs and alkyl iodides using m- or p-trifluoromethylstyrene as a reaction promotor and Ni(acac)(2) as a catalyst (7.5-10 mol %; -35 degrees C, 5-10 h) leading to a broad range of polyfunctional cross-coupling products'.

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页码：3544 / 3553

页数：10

相关论文

共 72 条

[1] THE SYNTHESIS OF THIOPHENIUM AND OF OXAZOLIUM SALTS FROM DIAZOKETONES [J].

ACHESON, RM ;

COOPER, MW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (05) :1185-1193

[2]

[Anonymous], 1991, COMPREHENSIVE ORGANI

[3] RADICAL REACTIONS IN SYNTHESIS - CARBON CARBON BOND FORMATION FROM 2-SUBSTITUTED ALLYL TRIALKYL STANNANES [J].

BALDWIN, JE ;

ADLINGTON, RM ;

BIRCH, DJ ;

CRAWFORD, JA ;

SWEENEY, JB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (17) :1339-1340

[4] FUNCTIONALIZED ETHYLENE OLIGOMERS AS PHASE-TRANSFER CATALYSTS [J].

BERGBREITER, DE ;

BLANTON, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5828-5833

[5] 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

[6] THE CHEMISTRY OF NITRILIUM SALTS .2. THE PREPARATION OF NITRILIUM TRIFLUOROMETHANESULPHONATE SALTS AND THEIR REACTIONS WITH SOME OXYGEN AND SULFUR NUCLEOPHILES [J].

BOOTH, BL ;

JIBODU, KO ;

PROENCA, JRP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (05) :1067-1073

[7] ORGANOMANGANESE (II) REAGENTS .16. COPPER-CATALYZED 1,4-ADDITION OF ORGANOMANGANESE CHLORIDES TO CONJUGATED ENONES [J].

CAHIEZ, G ;

ALAMI, M .

TETRAHEDRON LETTERS, 1989, 30 (27) :3541-3544

[8] ORGANOMANGANESE(II) REAGENTS .23. MANGANESE-CATALYZED ACYLATION OF ORGANOMAGNESIUM COMPOUNDS BY CARBOXYLIC-ACID CHLORIDES [J].

CAHIEZ, G ;

LABOUE, B .

TETRAHEDRON LETTERS, 1992, 33 (31) :4439-4442

[9] NEW DEVELOPMENTS IN PALLADIUM CATALYZED CROSS COUPLING - THE COUPLING OF ALKYL IODIDES WITH ALKYL GRIGNARD-REAGENTS [J].

CASTLE, PL ;

WIDDOWSON, DA .

TETRAHEDRON LETTERS, 1986, 27 (49) :6013-6016

[10]

CHANON M, 1982, B SOC CHIM FR II-CH, P197

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