NICKEL-CATALYZED CARBONYLATION OF ALPHA-KETO ALKYNES UNDER PHASE-TRANSFER CONDITIONS

被引：29

作者：

ARZOUMANIAN, H ^{[1
]}

JEAN, M ^{[1
]}

NUEL, D ^{[1
]}

CABRERA, A ^{[1
]}

GUTIERREZ, JLG ^{[1
]}

ROSAS, N ^{[1
]}

机构：

[1] NATL AUTONOMOUS UNIV MEXICO,INST QUIM,MEXICO CITY 04510,DF,MEXICO

来源：

ORGANOMETALLICS | 1995年 / 14卷 / 11期

关键词：

D O I：

10.1021/om00011a071

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

alpha-Keto alkynes are carbonylated in the presence of Ni(CN)(2) under phase transfer conditions (toluene, 5 N NaOH, tetrabutylammonium bromide) to give either unsaturated hydroxybutyrolactones or 2-alkynylidene 3-keto carboxylic acids depending on. the presence or absence of an alpha-H on the carbon alpha to the alkynyl group. This is rationalized, in the second case, by a rearrangement following abstraction of this alpha-H by base. A rearrangement to an allenic intermediate prior to carbonylation is excluded.

引用

页码：5438 / 5441

页数：4

共 29 条

[1] NOVEL NICKEL CATALYZED CONVERSION OF 2-BROMO-1-PHENYL-1,3-BUTADIENE TO AN ALPHA-KETO LACTONE - AN EXAMPLE OF DOUBLE CARBONYLATION OF A HALODIENE [J].

ALPER, H ;

VASAPOLLO, G .

TETRAHEDRON LETTERS, 1989, 30 (20) :2617-2618

[2] MILD, REGIOSPECIFIC BUT-2-ENOLIDE SYNTHESIS AND A CONVENIENT PREPARATION OF ACYLATED DIENES [J].

ALPER, H ;

CURRIE, JK ;

ABBAYES, HD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (07) :311-312

[3] FACILE OXIDATIVE CYCLIZATION AND CARBONYLATION OF ALLYLIC ALCOHOLS [J].

ALPER, H ;

LEONARD, D .

TETRAHEDRON LETTERS, 1985, 26 (46) :5639-5642

[4] SOLID-LIQUID PHASE-TRANSFER AND COBALT CATALYZED SYNTHESIS OF BUT-2-ENOLIDE [J].

ARZOUMANIAN, H ;

PETRIGNANI, JF .

TETRAHEDRON LETTERS, 1986, 27 (49) :5979-5980

[5] MONOCARBOXYLATION AND DICARBOXYLATION OF ALPHA-HALOALKYNES CATALYZED BY NICKEL CYANIDE UNDER PHASE-TRANSFER CONDITIONS [J].

ARZOUMANIAN, H ;

COCHINI, F ;

NUEL, D ;

PETRIGNANI, JF ;

ROSAS, N .

ORGANOMETALLICS, 1992, 11 (01) :493-495

[6] NICKEL-TRANSFER-CATALYZED AND PHASE-TRANSFER-CATALYZED CARBOXYLATION OF PROPARGYL AND ALLENYL HALIDES [J].

ARZOUMANIAN, H ;

COCHINI, F ;

NUEL, D ;

ROSAS, N .

ORGANOMETALLICS, 1993, 12 (05) :1871-1875

[7]

ARZOUMANIAN H, 1993, J MOL CATAL, V85, P285

[8]

Brandsma L., 1988, PREPARATIVE ACETYLEN

[9]

Colquhoun H. M., 1991, CARBONYLATION DIRECT

[10] ACYLPALLADATION OF INTERNAL ALKYNES AND PALLADIUM-CATALYZED CARBONYLATION OF (Z)-BETA-IODOENONES AND RELATED DERIVATIVES PRODUCING GAMMA-LACTONES AND GAMMA-LACTAMS [J].

COPERET, C ;

SUGIHARA, T ;

WU, GZ ;

SHIMOYAMA, I ;

NEGISHI, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) :3422-3431

← 1 2 3 →