Regiocontrolled Ru-catalyzed addition of carboxylic acids to alkynes: practical protocols for the synthesis of vinyl esters

被引：137

作者：

Goossen, LJ ^{[1
]}

Paetzold, J ^{[1
]}

Koley, D ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

CHEMICAL COMMUNICATIONS | 2003年 / 06期

关键词：

D O I：

10.1039/b211277a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The catalytic activity of commercially available, air and water stable ruthenium complexes in the addition of carboxylic acids to terminal alkynes was found to be drastically enhanced by the addition of small quantities of base. Moreover, the regioselectivity of the reaction can be controlled by the choice of the base so that both the Markovnikov (Na2CO3) and the anti-Markovnikov products (DMAP) are now easily accessible in excellent selectivities.

引用

页码：706 / 707

页数：2

共 30 条

[1] ENANTIOSELECTIVE HYDROFORMYLATION WITH THE CHIRAL BIDENTATE P,N-LIGAND 2-[1-(1S,2S,5R)-(-)MENTHOXYDIPHENYLPHOSPHINO]PYRIDINE CATIONIC RHODIUM(I) COMPLEXES [J].

ARENA, CG ;

NICOLO, F ;

DROMMI, D ;

BRUNO, G ;

FARAONE, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (19) :2251-2252

[2] RUTHENIUM-CATALYZED ADDITIONS TO ALKYNES - SYNTHESIS OF ACTIVATED ESTERS AND THEIR USE IN ACYLATION REACTIONS [J].

BRUNEAU, C ;

NEVEUX, M ;

KABOUCHE, Z ;

RUPPIN, C ;

DIXNEUF, PH .

SYNLETT, 1991, (11) :755-763

[3] Utilization of an industrial feedstock without separation - Ruthenium-catalysed hydrocarboxylation of propadiene and propyne [J].

Bruneau, C ;

Neveux-Duflos, M ;

Dixneuf, PH .

GREEN CHEMISTRY, 1999, 1 (04) :183-185

[4] REACTIONS OF ENOL ACETATES WITH THALLIUM(I) ACETATE-IODINE [J].

CAMBIE, RC ;

HAYWARD, RC ;

JURLINA, JL ;

RUTLEDGE, PS ;

WOODGATE, PD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (02) :126-130

[5]

CORT AD, 1991, J ORG CHEM, V56, P6708

[6] OLEFIN CYCLOPROPANATION REACTIONS CATALYZED BY NOVEL RUTHENACARBORANE CLUSTERS [J].

DEMONCEAU, A ;

SAIVE, E ;

DEFROIDMONT, Y ;

NOELS, AF ;

HUBERT, AJ ;

CHIZHEVSKY, IT ;

LOBANOVA, IA ;

BREGADZE, VI .

TETRAHEDRON LETTERS, 1992, 33 (15) :2009-2012

[7] Smart ruthenium catalysts for the selective catalytic transformations of alkynes [J].

Dixneuf, PH ;

Bruneau, C ;

Derien, S .

PURE AND APPLIED CHEMISTRY, 1998, 70 (05) :1065-1070

[8] STEREOSELECTIVE SYNTHESIS OF Z-ENOL ESTERS CATALYZED BY [BIS(DIPHENYLPHOSPHINO)ALKANE]BIS(2-METHYLPROPENYL)RUTHENIUM COMPLEXES [J].

DOUCET, H ;

HOFER, J ;

BRUNEAU, C ;

DIXNEUF, PH .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (10) :850-851

[9] GENERAL-SYNTHESIS OF (Z)-ALK-1-EN-1-YL ESTERS VIA RUTHENIUM-CATALYZED ANTI-MARKOVNIKOV TRANS-ADDITION OF CARBOXYLIC-ACIDS TO TERMINAL ALKYNES [J].

DOUCET, H ;

MARTINVACA, B ;

BRUNEAU, C ;

DIXNEUF, PH .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7247-7255

[10]

Doucet H, 1997, SYNLETT, P807

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