Gold-Catalyzed Simultaneous Formation of C-C, C=O, and C-F bonds in the Presence of Selectfluor: A Synthesis of Fluoroindenes from Allene Esters

被引：47

作者：

Liu, Yunkui ^{[1
,2
]}

Zhu, Jie ^{[1
]}

Qian, Jianqiang ^{[1
]}

Xu, Zhenyuan ^{[1
]}

机构：

[1] Zhejiang Univ Technol, State Key Lab Breeding Base Green Chem Synth Tech, Hangzhou 310014, Zhejiang, Peoples R China

[2] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325027, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 12期

关键词：

GOLD(I)-CATALYZED INTRAMOLECULAR HYDROARYLATION; ELECTROPHILIC FLUORINATION; ORGANOGOLD COMPOUNDS; ALKYNES; INDENE; AMINOFLUORINATION; REARRANGEMENT; CYCLIZATIONS; REACTIVITY; SYSTEM;

D O I：

10.1021/jo3006528

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach for the synthesis of fluorinated indene derivatives has been developed via a gold-catalyzed three-component tandem reaction between allene esters, Selectfluor, and water.

引用

页码：5411 / 5417

页数：7

共 51 条

[1] Gold-catalyzed decorations of arenes and heteroarenes with C-C multiple bonds [J].

Bandini, Marco .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (03) :1358-1367

[2] Gold-mediated C-H bond functionalisation [J].

Boorman, Tanya C. ;

Larrosa, Igor .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1910-1925

[3] Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions [J].

Corma, A. ;

Leyva-Perez, A. ;

Sabater, Maria J. .

CHEMICAL REVIEWS, 2011, 111 (03) :1657-1712

[4] Stereoselective construction of fluorinated indanone derivatives via a triple cascade Lewis acid-catalyzed reaction [J].

Cui, Han-Feng ;

Dong, Ke-Yan ;

Zhang, Guang-Wu ;

Wang, Lian ;

Ma, Jun-An .

CHEMICAL COMMUNICATIONS, 2007, (22) :2284-2286

[5] Gold Catalysis: Hydrolysis of Di(alkoxy)carbenium Ion Intermediates as a Sensor for the Electronic Properties of Gold(I) Complexes [J].

Doepp, Rene ;

Lothschuetz, Christian ;

Wurm, Thomas ;

Pernpointner, Markus ;

Keller, Sascha ;

Rominger, Frank ;

Hashmi, A. Stephen K. .

ORGANOMETALLICS, 2011, 30 (21) :5894-5903

[6] FLUORINE SUBSTITUENT EFFECTS ON THERMAL ISOMERIZATIONS - A NEW THERMAL-REACTION OF 1,3,5-HEXATRIENES [J].

DOLBIER, WR ;

PALMER, K ;

KORONIAK, H ;

ZHANG, HQ ;

GOEDKIN, VL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1059-1060

[7] THERMAL REARRANGEMENTS OF 9,10-BIS(TRIFLUOROVINYL)PHENANTHRENE [J].

DOLBIER, WR ;

PALMER, KW .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :7064-7069

[8]

Falletta E., 2012, MODERN GOLD CATALYZE, P309

[9] C-C coupling reactions of superstrong CF3 groups with C(sp2)-H bonds:: Reactivity and synthetic utility of zero-valent niobium catalyst [J].

Fuchibe, Kohei ;

Mitomi, Ken ;

Suzuki, Ryo ;

Akiyama, Takahiko .

CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (02) :261-271

[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 →