Iron-catalyzed trifluoromethylation of vinylcyclopropanes: facile synthesis of CF3-containing dihydronaphthalene derivatives

被引:35
作者
Li, Zong-Rui [1 ,2 ]
Bao, Xing-Xing [3 ,4 ]
Sun, Jian [1 ,2 ]
Shen, Jing [1 ,2 ]
Wu, Dun-Qi [1 ,2 ]
Liu, Yan-Kai [1 ,2 ]
Deng, Qing-Hai [1 ,2 ]
Liu, Feng [3 ,4 ]
机构
[1] Shanghai Normal Univ, Educ Minist, Key Lab Resource Chem, Shanghai 200234, Peoples R China
[2] Shanghai Normal Univ, Shanghai Key Lab Rare Earth Funct Mat, Shanghai 200234, Peoples R China
[3] Soochow Univ, Jiangsu Key Lab Translat Res & Therapy Neuropsych, 199 Ren Ai Rd, Suzhou 215123, Jiangsu, Peoples R China
[4] Soochow Univ, Dept Med Chem, Coll Pharmaceut Sci, 199 Ren Ai Rd, Suzhou 215123, Jiangsu, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2016年 / 3卷 / 08期
基金
中国国家自然科学基金;
关键词
PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; BOND-FORMATION; OXIDATIVE TRIFLUOROMETHYLATION; ELECTROPHILIC TRIFLUOROMETHYLATION; BIOLOGICAL EVALUATION; CARBONYL-COMPOUNDS; GENERAL-SYNTHESIS; TERMINAL ALKENES; COPPER; FLUORINATION;
D O I
10.1039/c6qo00166a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient Fe(II)-catalyzed trifluoromethylation of vinylcyclopropanes was successfully developed. A series of CF3-containing dihydronaphthalene derivatives were prepared in moderate to high yields (up to 96%) under mild reaction conditions using the Togni reagent as the CF3 source.
引用
收藏
页码:934 / 938
页数:5
相关论文
共 98 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]   Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes [J].
Alonso, Concepcion ;
Martinez de Marigorta, Eduardo ;
Rubiales, Gloria ;
Palacios, Francisco .
CHEMICAL REVIEWS, 2015, 115 (04) :1847-1935
[3]   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
[4]   On the Role of Metal Contaminants in Catalyses with FeCl3 [J].
Buchwald, Stephen L. ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) :5586-5587
[5]   Synthesis and biological evaluation of new selective cytotoxic cyclolignans derived from podophyllotoxin [J].
Castro, MA ;
del Corral, JMM ;
Gordaliza, M ;
García, PA ;
Gómez-Zurita, MA ;
García-Grdvalos, MD ;
de la Iglesia-Vicente, J ;
Gajate, C ;
An, FY ;
Mollinedo, F ;
San Feliciano, A .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (05) :1214-1222
[6]   Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents [J].
Charpentier, Julie ;
Frueh, Natalja ;
Togni, Antonio .
CHEMICAL REVIEWS, 2015, 115 (02) :650-682
[7]  
Chen P., 2013, SYNTHESIS-STUTTGART, P2919
[8]   Copper-Catalyzed Tandem Trifluoromethylation/Semipinacol Rearrangement of Allylic Alcohols [J].
Chen, Zhi-Min ;
Bai, Wei ;
Wang, Shao-Hua ;
Yang, Bin-Miao ;
Tu, Yong-Qiang ;
Zhang, Fu-Min .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) :9781-9785
[9]   The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates [J].
Cho, Eun Jin ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2011, 13 (24) :6552-6555
[10]   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