Synthesis of Fluorine-Containing Multisubstituted Phenanthridines by Rhodium-Catalyzed Alkyne [2+2+2] Cycloaddition and Tandem sp2 CH Difluoromethylenation

被引：36

作者：

Li, Yajun ^{[1
,2
]}

Zhu, Jiangtao ^{[2
]}

Zhang, Lisi ^{[2
]}

Wu, Yongming ^{[2
]}

Gong, Yuefa ^{[1
]}

机构：

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

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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 25期

基金：

美国国家科学基金会;

关键词：

cycloaddition; fluorine; homogeneous catalysis; polycycles; rhodium; ONE-POT SYNTHESIS; CONSTRUCTION; DERIVATIVES; COMPLEXES; PYRIDINES; BOND; CYCLOTRIMERIZATION; CYCLIZATION; ARYLATION; EFFICIENT;

D O I：

10.1002/chem.201300288

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly efficient method for the synthesis of fluorine-containing multisubstituted phenanthridines through Rh-catalyzed alkyne [2+2+2] cycloaddition reactions has been developed. This method exhibits excellent functional-group compatibility. When a bromodifluoromethyl group, rather than a trifluoromethyl group, was employed in the cycloaddition reaction, more-complicated polycyclic compounds were obtained through tandem Rh-catalyzed cycloaddition/CH difluoromethylenation. This route provides convenient access to fluorine-containing polycyclic compounds.

引用

页码：8294 / 8299

页数：6

共 58 条

[1]

[Anonymous], 2009, ANGEW CHEM INT ED, V48, P2830

[2]

[Anonymous], 2002, ANGEW CHEM INT ED, V41, P3281

[3]

[Anonymous], 2009, ANGEW CHEM INT EDIT, V48, P5470

[4]

[Anonymous], 2009, Angew. Chem

[5]

[Anonymous], 2009, ANGEW CHEM INT ED, V48, P6713

[6]

[Anonymous], 2009, ANGEW CHEM INT ED, V48, P572

[7] Electron-Transfer-Mediated Synthesis of Phenanthridines by Intramolecular Arylation of Anions from N-(ortho-Halobenzyl)arylamines: Regiochemical and Mechanistic Analysis [J].

Buden, Maria E. ;

Dorn, Viviana B. ;

Garnba, Martina ;

Pierini, Adriana B. ;

Rossi, Roberto A. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (07) :2206-2218

[8]

Ca N. D., 2010, ADV SYNTH CATAL, V352, P1451

[9]

Candito D.A., 2009, Angew. Chem, V121, P6841

[10] Palladium-Catalyzed Synthesis of 2-Fluoroalkyl-3-methylene-3H-indoles Through a Domino Carbopalladation/C-H Activation Process [J].

Chen, Zixian ;

Zhu, Jiangtao ;

Xie, Haibo ;

Li, Shan ;

Wu, Yongming ;

Gong, Yuefa .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (2-3) :325-330

← 1 2 3 4 5 6 →