Iron(II)-Catalyzed Trifluoromethylation of Potassium Vinyltrifluoroborates

被引:199
作者
Parsons, Andrew T. [1 ]
Senecal, Todd D. [1 ]
Buchwald, Stephen L. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
fluorine; homogeneous catalysis; iron; trifluoromethylation; COPPER-CATALYZED TRIFLUOROMETHYLATION; ENANTIOSELECTIVE ALPHA-TRIFLUOROMETHYLATION; ELECTROPHILIC TRIFLUOROMETHYLATION; MEDIATED TRIFLUOROMETHYLATION; ALLYLIC TRIFLUOROMETHYLATION; ARYL FLUORIDES; BORONIC ACIDS; REAGENT; PERFLUOROALKYLATION; ORGANOCATALYSIS;
D O I
10.1002/anie.201108267
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Exchanging BF 3 by CF 3: The title reaction proceeds under exceedingly mild reaction conditions and provides 2-arylvinyl- and 2-heteroarylvinyl-substituted substrates with E/Z selectivities of more than 95:5. Experimental observations suggest that the reaction does not proceed through a transmetalation of the RBF 3K species to the iron catalyst. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:2947 / 2950
页数:4
相关论文
共 40 条
[1]   The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes [J].
Allen, Anna E. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) :4986-+
[2]  
[Anonymous], 2009, Angew. Chem., Int. Ed.
[3]   The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates [J].
Cho, Eun Jin ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2011, 13 (24) :6552-6555
[4]   The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides [J].
Cho, Eun Jin ;
Senecal, Todd D. ;
Kinzel, Tom ;
Zhang, Yong ;
Watson, Donald A. ;
Buchwald, Stephen L. .
SCIENCE, 2010, 328 (5986) :1679-1681
[5]   Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids [J].
Chu, Lingling ;
Qing, Feng-Ling .
ORGANIC LETTERS, 2010, 12 (21) :5060-5063
[6]   Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me3SiCF3 [J].
Chu, Lingling ;
Qing, Feng-Ling .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7262-+
[7]   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
[8]   Mild electrophilic trifluoromethylation of secondary and primary aryl- and alkylphosphines using hypervalent iodine(III)-CF3 reagents [J].
Eisenberger, Patrick ;
Kieltsch, Iris ;
Armanino, Nicolas ;
Togni, Antonio .
CHEMICAL COMMUNICATIONS, 2008, (13) :1575-1577
[9]   Reactivity of a Hypervalent Iodine Trifluoromethylating Reagent toward THF: Ring Opening and Formation of Trifluoromethyl Ethers [J].
Fantasia, Serena ;
Welch, Jan M. ;
Togni, Antonio .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) :1779-1782
[10]   Organocatalyzed Regio- and Enantioselective Allylic Trifluoromethylation of Morita-Baylis-Hillman Adducts Using Ruppert-Prakash Reagent [J].
Furukawa, Tatsuya ;
Nishimine, Takayuki ;
Tokunaga, Etsuko ;
Hasegawa, Kimiko ;
Shiro, Motoo ;
Shibata, Norio .
ORGANIC LETTERS, 2011, 13 (15) :3972-3975