Iodide acceleration in the Pd-catalyzed coupling of aromatic 1,2-ditriflates with alkynes: Synthesis of enediynes

被引：63

作者：

Powell, NA ^{[1
]}

Rychnovsky, SD ^{[1
]}

机构：

[1] UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92697

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 44期

关键词：

aromatic ditriflates; aryl enediyne; alkyne; Hagihara reaction; Pd cross-coupling;

D O I：

10.1016/0040-4039(96)01698-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryl enediynes have been synthesized in a one-pot procedure by a Pd-catalyzed coupling of terminal alkynes and ortho-aryl ditriflates. A variety of substrates have been examined. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：7901 / 7904

页数：4

共 26 条

[1] AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL AND ARYL HALIDES OR TRIFLATES WITH TERMINAL ALKYNES [J].

ALAMI, M ;

FERRI, F ;

LINSTRUMELLE, G .

TETRAHEDRON LETTERS, 1993, 34 (40) :6403-6406

[2] INTIMATE MECHANISM OF OXIDATIVE ADDITION TO ZEROVALENT PALLADIUM COMPLEXES IN THE PRESENCE OF HALIDE-IONS AND ITS RELEVANCE TO THE MECHANISM OF PALLADIUM-CATALYZED NUCLEOPHILIC SUBSTITUTIONS [J].

AMATORE, C ;

JUTAND, A ;

SUAREZ, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9531-9541

[3] ROLE AND EFFECTS OF HALIDE-IONS ON THE RATES AND MECHANISMS OF OXIDATIVE ADDITION OF IODOBENZENE TO LOW-LIGATED ZEROVALENT PALLADIUM COMPLEXES PD0(PPH3)2 [J].

AMATORE, C ;

AZZABI, M ;

JUTAND, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8375-8384

[4] REACTIVE 1,4-DEHYDROAROMATICS [J].

BERGMAN, RG .

ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (01) :25-31

[5] CDPI3-ENEDIYNE AND CDPI3-EDTA CONJUGATES - A NEW CLASS OF DNA CLEAVING AGENTS [J].

BOGER, DL ;

ZHOU, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :3018-3024

[6] PALLADIUM-CATALYZED REACTION OF PHENYL FLUOROALKANESULFONATES WITH ALKYNES AND ALKENES [J].

CHEN, QY ;

YANG, ZY .

TETRAHEDRON LETTERS, 1986, 27 (10) :1171-1174

[7] THE TANDEM BERGMAN-RADICAL CYCLIZATION - A NEW METHOD FOR RING ANNULATION [J].

GRISSOM, JW ;

CALKINS, TL .

TETRAHEDRON LETTERS, 1992, 33 (17) :2315-2318

[8] ARYL RADICAL ADDITIONS TO ALDEHYDES AND OXIME ETHERS - THE TANDEM ENEDIYNE-RADICAL CYCLIZATION [J].

GRISSOM, JW ;

KLINGBERG, D .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6559-6564

[9] KINETIC AND MECHANISTIC STUDIES OF THE TANDEM ENEDIYNE-RADICAL CYCLIZATION [J].

GRISSOM, JW ;

CALKINS, TL .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5422-5427

[10] HIGH-TEMPERATURE RADICAL CYCLIZATION ANOMALIES IN THE TANDEM ENEDIYNE-BIS-RADICAL CYCLIZATION [J].

GRISSOM, JW ;

CALKINS, TL ;

HUANG, DH ;

MCMILLEN, H .

TETRAHEDRON, 1994, 50 (16) :4635-4650

← 1 2 3 →