Copper-Catalyzed Cascade Cyclization for the Synthesis of Trifluoromethyl-Substituted Spiro-2H-azirines from 1,6-Enynes

被引：36

作者：

He, Yu-Tao ^{[1
]}

Wang, Qiang ^{[1
]}

Zhao, Jiahui ^{[1
]}

Wang, Xiao-Zhen ^{[1
]}

Qiu, Yi-Feng ^{[1
]}

Yang, Yu-Chen ^{[1
]}

Hu, Jing-Yuan ^{[1
]}

Liu, Xue-Yuan ^{[1
]}

Liang, Yong-Min ^{[1
,2
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Solid Lubricat, Lanzhou 730000, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 14-15期

关键词：

2H-azirines; cascade cyclization; copper enynes; spirocyclic skeleton; BOND-FORMATION; REDUCTIVE ELIMINATION; 2H-AZIRINES; ALKENES; EFFICIENT; OXYTRIFLUOROMETHYLATION; ARYLTRIFLUOROMETHYLATION; PYRIDINES; ENYNES; CUCF3;

D O I：

10.1002/adsc.201500510

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A method for the synthesis of trifluoromethyl CF3-substituted spirocyclic compounds containing with a unique quaternary carbon center from readily available starting materials has been developed. The reaction provides a facile access to 2H-azirines via cascade cyclization. These compounds constitute a new class of functionalized synthetic intermediates, which can be used for the synthesis of various nitrogen-containing heterocycles and biologically active CF3-containing compounds.

引用

页码：3069 / 3075

页数：7

共 71 条

[1]

[Anonymous], 2007, ANGEW CHEM, DOI DOI 10.1103/PHYSREVLETT.112.077206

[2] Mechanistic and Computational Studies of Oxidatively-Induced Aryl-CF3 Bond-Formation at Pd: Rational Design of Room Temperature Aryl Trifluoromethylation [J].

Ball, Nicholas D. ;

Gary, J. Brannon ;

Ye, Yingda ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (19) :7577-7584

[3] Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV) [J].

Ball, Nicholas D. ;

Kampf, Jeff W. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) :2878-+

[4]

Berkowitz W. F., 2011, ORG REACTIONS, V78, P321

[5] Exploiting the Chemistry of Strained Rings: Synthesis of Indoles via Domino Reaction of Aryl Iodides with 2H-Azirines [J].

Candito, David A. ;

Lautens, Mark .

ORGANIC LETTERS, 2010, 12 (15) :3312-3315

[6] Rhodium-Catalyzed Carbocyclization and Chlorosulfonylation of 1,6-Enynes with Sulfonyl Chlorides [J].

Chen, Chen ;

Su, Jianhua ;

Tong, Xiaofeng .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (16) :5014-5018

[7] Rh(II)-catalyzed isomerization of 2-Aryl-2H-azirines to 2,3-disubstituted indoles [J].

Chiba, Shunsuke ;

Hattori, Gaku ;

Narasaka, Koichi .

CHEMISTRY LETTERS, 2007, 36 (01) :52-53

[8] Copper-Catalyzed Oxidative Trifluoromethylation of Terminal Alkenes Using Nucleophilic CF3SiMe3: Efficient C(sp3)-CF3 Bond Formation [J].

Chu, Lingling ;

Qing, Feng-Ling .

ORGANIC LETTERS, 2012, 14 (08) :2106-2109

[9]

Egami H., 2013, ANGEW CHEM, V125, P7995

[10] Trifluoromethylation Reactions for the Synthesis of β-Trifluoromethylamines [J].

Egami, Hiromichi ;

Kawamura, Shintaro ;

Miyazaki, Ayako ;

Sodeoka, Mikiko .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (30) :7841-7844

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