Pd-Catalyzed Stereoselective Carboperfluoroalkylation of Alkynes

被引：191

作者：

Li, Zhaodong ^{[1
]}

Garcia-Dominguez, Andres ^{[1
]}

Nevado, Cristina ^{[1
]}

机构：

[1] Univ Zurich, Dept Chem, CH-8057 Zurich, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 36期

基金：

瑞士国家科学基金会; 欧洲研究理事会;

关键词：

CROSS-COUPLING REACTIONS; COPPER-MEDIATED DIFLUOROMETHYLATION; LIGHT PHOTOREDOX CATALYSIS; RADICAL (PHENYLSULFONYL)DIFLUOROMETHYLATION; ELECTROPHILIC TRIFLUOROMETHYLATION; ETHYL BROMODIFLUOROACETATE; ACTIVATED ALKENES; GRIGNARD-REAGENTS; VINYL IODIDES; ATOM-TRANSFER;

D O I：

10.1021/jacs.5b07432

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Pd-catalyzed three component reaction involving terminal alkynes, boronic acids, and perfluoralkyl iodides is presented here. Trisubstituted perfluoro-alkenes can be obtained in a highly regio- and stereocontrolled manner by the simultaneous addition of both aryl and CnFm groups across the triple bond in a radical-mediated process. The reaction is operationally simple offering a broad scope and functional group tolerance.

引用

收藏

页码：11610 / 11613

页数：4

相关论文

共 69 条

[1] Ni(II)-Catalyzed Oxidative Coupling between C(sp2)-H in Benzamides and C(sp3)-H in Toluene Derivatives [J].

Aihara, Yoshinori ;

Tobisu, Mamoru ;

Fukumoto, Yoshiya ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (44) :15509-15512

[2]

[Anonymous], 2015, ANGEW CHEM

[3] Recent Progress in Direct Introduction of Fluorinated Groups on Alkenes and Alkynes by means of C-H Bond Functionalization [J].

Besset, Tatiana ;

Poisson, Thomas ;

Pannecoucke, Xavier .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (51) :16830-16845

[4] Tamed Arene and Heteroarene Trifluoromethylation [J].

Besset, Tatiana ;

Schneider, Cedric ;

Cahard, Dominique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5048-5050

[5]

CHEN QY, 1985, ACTA CHIM SINICA, V43, P1118

[6] STUDIES ON FLUOROALKYLATION AND FLUOROALKOXYLATION .28. PALLADIUM(O)-INDUCED ADDITION OF FLUOROALKYL IODIDES TO ALKENES - AN ELECTRON-TRANSFER PROCESS [J].

CHEN, QY ;

YANG, ZY ;

ZHAO, CX ;

QIU, ZM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (03) :563-567

[7] Hydrotrifluoromethylation and iodotrifluoromethylation of alkenes and alkynes using an inorganic electride as a radical generator [J].

Choi, Sungkyu ;

Kim, Ye Ji ;

Kim, Sun Min ;

Yang, Jung Woon ;

Kim, Sung Wng ;

Cho, Eun Jin .

NATURE COMMUNICATIONS, 2014, 5

[8] Oxytrifluoromethylation of multiple bonds using copper catalyst under mild conditions [J].

Egami, Hiromichi ;

Shimizu, Ryo ;

Sodeoka, Mikiko .

TETRAHEDRON LETTERS, 2012, 53 (41) :5503-5506

[9] Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation [J].

Eisenberger, P ;

Gischig, S ;

Togni, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (09) :2579-2586

[10] Stereoselective synthesis of cyclic ethers using vinylogous sulfonates as radical accepters:: Effect of E/Z geometry and temperature on diastereoselectivity [J].

Evans, PA ;

Manangan, T .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4523-4528

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