Au(I)-Catalyzed Intramolecular Hydroamination of the Fluorinated N′-Aryl-N-Propargyl Amidines: Mild Conditions for the Synthesis of 2-Fluoroalkyl Imidazole Derivatives

被引：57

作者：

Li, Shan ^{[1
]}

Li, Zhengke ^{[1
]}

Yuan, Yafen ^{[1
]}

Peng, Dongjie ^{[1
]}

Li, Yajun ^{[1
,2
]}

Zhang, Lisi ^{[1
]}

Wu, Yongming ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[2] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Wuhan 430074, Hubei, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 04期

基金：

美国国家科学基金会;

关键词：

GOLD-CATALYZED CYCLIZATION; ONE-POT SYNTHESIS; C BOND FORMATION; ALKYNES; OXAZOLES; ALKENES; 2,3,4,5-TETRAHYDROPYRIDINES; CYCLOISOMERIZATION; 5-ALKYNYLAMINES; HETEROCYCLES;

D O I：

10.1021/ol3000525

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The gold(I)-catalyzed synthesis of 2-fluoroalkyl imidazole derivatives was developed. Catalyzed by gold(I), propargyl amidines underwent a 5-exo-dig cyclization to afford 2-fluoroalkyl-5-methyl imidazoles. Also, 2-fluoroalkyl imidazole-5-carbaldehydes were obtained in the presence of NIS. A mechanism investigation manifested the probable process and the carbonyl oxygen derived from O-2.

引用

页码：1130 / 1133

页数：4

共 52 条

[1] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[2] Gold-catalyzed cycloisomerization of alk-4-yn-1-ones [J].

Belting, Volker ;

Krause, Norbert .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (06) :1221-1225

[3]

Benitez D, 2009, NAT CHEM, V1, P482, DOI [10.1038/NCHEM.331, 10.1038/nchem.331]

[4] Gold-Catalyzed Intramolecular Aminoarylation of Alkenes: C-C Bond Formation through Bimolecular Reductive Elimination [J].

Brenzovich, William E., Jr. ;

Benitez, Diego ;

Lackner, Aaron D. ;

Shunatona, Hunter P. ;

Tkatchouk, Ekaterina ;

Goddard, William A., III ;

Toste, F. Dean .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) :5519-5522

[5] Domino gold-catalyzed rearrangement and fluorination of propargyl acetates [J].

de Haro, Teresa ;

Nevado, Cristina .

CHEMICAL COMMUNICATIONS, 2011, 47 (01) :248-249

[6] Gold-Catalyzed Synthesis of α-Fluoro Acetals and α-Fluoro Ketones from Alkynes [J].

de Haro, Teresa ;

Nevado, Cristina .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (16) :2767-2772

[7]

ELOY F, 1973, CHIM THER, V8, P437

[8]

FUKUDA Y, 1987, HETEROCYCLES, V25, P297

[9]

FUKUDA Y, 1991, SYNTHESIS-STUTTGART, P975

[10] Gold-Catalyzed Cross-Couplings: New Opportunities for C-C Bond Formation [J].

Garcia, Pierre ;

Malacria, Max ;

Aubert, Corinne ;

Gandon, Vincent ;

Fensterbank, Louis .

CHEMCATCHEM, 2010, 2 (05) :493-497

← 1 2 3 4 5 6 →