Palladium-catalysed hydroarylation and hydrovinylation of 3,3-dialkoxy-1-aryl-1-propynes. An approach to 3-aryl- and 3-vinylquinolines

被引：69

作者：

Cacchi, S ^{[1
]}

Fabrizi, G ^{[1
]}

Marinelli, F ^{[1
]}

Moro, L ^{[1
]}

Pace, P ^{[1
]}

机构：

[1] UNIV STUDI V VETOIO,DIPARTIMENTO CHIM INGN CHIM & MAT,I-67100 LAQUILA,ITALY

来源：

TETRAHEDRON | 1996年 / 52卷 / 30期

关键词：

D O I：

10.1016/0040-4020(96)00557-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acetylenic acetals and ketals have been reacted with aryl and vinyl halides to generate hydroarylation and hydrovinylation products. The reaction proceeds with high regioselectivity. The carbopalladation step appears to be mainly controlled by steric effects and the new carbon-carbon bond is generated preferentially on the carbon bearing the acetal group. The reaction has been employed to develop a regioselective synthesis of 3-aryl and 3-vinylquinolines. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：10225 / 10240

页数：16

共 30 条

[1] PALLADIUM-CATALYZED REDUCTIVE ADDITION OF ARYL IODIDES TO ARYL AND ALKYLETHYNYLSILANES - A STEREO AND REGIOSELECTIVE ROUTE TO FUNCTIONALIZED 2,2-DISUBSTITUTED VINYLSILANES [J].

ARCADI, A ;

CACCHI, S ;

MARINELLI, F .

TETRAHEDRON LETTERS, 1986, 27 (52) :6397-6400

[2] The palladium-catalysed vinylic substitution of vinyl triflates with beta-substituted-alpha,beta-unsaturated carbonyl compounds. An application to the synthesis of cardenolides. [J].

Arcadi, A ;

Cacchi, S ;

Fabrizi, G ;

Marinelli, F ;

Pace, P .

TETRAHEDRON, 1996, 52 (20) :6983-6996

[3]

ARCADI A, 1986, GAZZ CHIM ITAL, V116, P725

[4] PALLADIUM-CATALYZED STEREOSELECTIVE HYDROVINYLATION OF DISUBSTITUTED ACETYLENES - PREPARATION OF FUNCTIONALIZED 1,2,4-TRISUBSTITUTED-1,3-DIENES [J].

ARCADI, A ;

BERNOCCHI, E ;

BURINI, A ;

CACCHI, S ;

MARINELLI, F ;

PIETRONI, B .

TETRAHEDRON LETTERS, 1989, 30 (26) :3465-3468

[5] THE PALLADIUM-CATALYZED REDUCTIVE ADDITION OF ARYL IODIDES TO PROPARGYL ALCOHOLS - A ROUTE TO GAMMA,GAMMA-DIARYL ALLYLIC ALCOHOLS [J].

ARCADI, A ;

CACCHI, S ;

MARINELLI, F .

TETRAHEDRON, 1985, 41 (22) :5121-5131

[6] THE PALLADIUM-TRIBUTYLAMMONIUM FORMATE REAGENT IN THE STEREOSELECTIVE HYDROGENATION, AND STEREOSELECTIVE AND REGIOSELECTIVE HYDROARYLATION OF ALKYL 4-HYDROXY-2-ALKYNOATES - A ROUTE TO SUBSTITUTED BUTENOLIDES [J].

ARCADI, A ;

BERNOCCHI, E ;

BURINI, A ;

CACCHI, S ;

MARINELLI, F ;

PIETRONI, B .

TETRAHEDRON, 1988, 44 (02) :481-490

[7]

BEYDOUN N, 1990, SYNTHESIS-STUTTGART, P729

[8] PALLADIUM CATALYZED TANDEM CYCLIZATION ANION CAPTURE PROCESSES - HYDRIDE ION CAPTURE BY VINYLPALLADIUM SPECIES [J].

BURNS, B ;

GRIGG, R ;

SRIDHARAN, V ;

WORAKUN, T .

TETRAHEDRON LETTERS, 1988, 29 (34) :4325-4328

[9] ALKYNE ACTIVATION BY ELECTROPHILIC [(ETA-C-5ME(5))RU(NO)(R)]+ (R=ME, PH, P-TOLYL) FRAGMENTS - BETA-MIGRATORY INSERTION, ISOMERIZATION, AND METALLACYCLE FORMATION [J].

BURNS, RM ;

HUBBARD, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (21) :9514-9520

[10] THE PALLADIUM-CATALYZED REACTION OF ARYL IODIDES WITH MONOSUBSTITUTED AND DISUBSTITUTED ACETYLENES - A NEW SYNTHESIS OF TRISUBSTITUTED ALKENES [J].

CACCHI, S ;

FELICI, M ;

PIETRONI, B .

TETRAHEDRON LETTERS, 1984, 25 (29) :3137-3140

← 1 2 3 →