Gold-catalyzed hydroarylation of alkynes

被引：328

作者：

Reetz, MT ^{[1
]}

Sommer, K ^{[1
]}

机构：

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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 18期

关键词：

homogeneous catalysis; gold; alkynes; aromatic substitution; C-H activation; CARBON-HYDROGEN-BONDS; C-H BONDS; ASYMMETRIC ALDOL REACTION; AROMATIC-SUBSTITUTION; ACTIVATION; OLEFINS; COMPLEXES; ARENES; TRANSFORMATION; ALKENYLATION;

D O I：

10.1002/ejoc.200300260

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hydroarylation of aryl-substituted alkynes by substituted electron-rich arenes is catalyzed by AuCl3 activated by such silver salts as AgSbF6. In the case of terminal alkynes, complete regioselectivity in favor of the 1,1-disubstituted olefin is observed. In the case of electron-poor alkynes such as acetylenecarboxylic acid ester, gold(I) complexes such as [Ph3PAuCl] activated by Ag salts or BF3.OEt2 are the best catalysts, resulting in opposite regioselectivity and high degrees of (Z) -selectivity. (C) Wiley-VCH Verlag GmbH Co.

引用

页码：3485 / 3496

页数：12

共 76 条

[1]

[Anonymous], ANGEW CHEM

[2] Gold catalysis in the reactions of 1,3-dicarbonyls with nucleophiles [J].

Arcadi, A ;

Bianchi, G ;

Di Giuseppe, S ;

Marinelli, F .

GREEN CHEMISTRY, 2003, 5 (01) :64-67

[3]

Arcadi A, 2001, ADV SYNTH CATAL, V343, P443, DOI 10.1002/1615-4169(200107)343:5<443::AID-ADSC443>3.3.CO

[4]

2-R

[5] AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].

Asao, N ;

Takahashi, K ;

Lee, S ;

Kasahara, T ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651

[6] MECHANISMS OF EPOXIDATION DURING OZONATION OF CARBON-CARBON DOUBLE-BONDS [J].

BAILEY, PS ;

HWANG, HH ;

CHIANG, CY .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (02) :231-234

[7]

BECKER HGO, 1996, ORGANIKUM, P442

[8] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].

Boele, MDK ;

van Strijdonck, GPF ;

de Vries, AHM ;

Kamer, PCJ ;

de Vries, JG ;

van Leeuwen, PWNM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587

[9] Gold: a relatively new catalyst [J].

Bond, GC .

CATALYSIS TODAY, 2002, 72 (1-2) :5-9

[10] Alkyne oxidations by cis-dioxoruthenium(VI) complexes.: A formal [3+2] cycloaddition reaction of alkynes with cis-[(Cn*)(CF3CO2)RuVIO2]ClO4 (Cn*=1,4,7-trimethyl-1,4,7-triazacyclononane) [J].

Che, CM ;

Yu, WY ;

Chan, PM ;

Cheng, WC ;

Peng, SM ;

Lau, KC ;

Li, WK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) :11380-11392

← 1 2 3 4 5 6 7 8 →