Palladium-Catalyzed C(sp3)-Si Bonds Transformation for Constructing Trifluoropropyl (Hetero)arenes through C(sp3)-C(sp2) Cross-Coupling Reactions

被引:0
作者
Liu Junjun [1 ]
Lu Taotao [1 ]
Ma Ping [1 ]
Zhao Qingyang [1 ]
Yee, Kwong Fuk [2 ]
机构
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci Shenzhen, Shenzhen Campus, Shenzhen 518107, Guangdong, Peoples R China
[2] Chinese Univ Hong Kong, Dept Chem, Hong Kong, Peoples R China
关键词
palladium catalysis; Hiyama cross-coupling reaction; fluoroalkylation; organosilicon; PROMOTED TRIFLUOROMETHYLATION; ORGANOSILICON COMPOUNDS; ARYL; METHYLATION; ACTIVATION; FLUORINE; ALKENES; ALKYNES; TRENDS; SALTS;
D O I
10.6023/cjoc202310013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed C(sp(3))- Si bonds transformation of commercially available polyalkoxy trifluorosilane reagents has been developed through C(sp(3))-C(sp(2)) cross-coupling reactions. This Hiyama cross-coupling reaction shows good functional group tolerance and provides a series of trifluoropropyl (hetero)arenes. The fluoride source and alkyl tether of bisphosphine ligand play important roles in improving yields.
引用
收藏
页码:1319 / 1326
页数:8
相关论文
共 60 条
[1]   Recent trends in dehydroxylative trifluoro-methylation, -methoxylation, -methylthiolation, and -methylselenylation of alcohols [J].
Cao, Yan ;
Ahmadi, Roya ;
Poor Heravi, Mohammad Reza ;
Issakhov, Alibek ;
Ebadi, Abdol Ghaffar ;
Vessally, Esmail .
RSC ADVANCES, 2021, 11 (62) :39593-39606
[2]   Advances in the Transition Metal-Free C-H Trifluoromethylation [J].
Chen, Demao ;
Jiang, Jianwen ;
Wan, Jie-Ping .
CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (21) :2582-2594
[3]   Recent Advances in Transition Metal-Promoted Trifluoromethylation Reactions [J].
Chen, Donghan ;
Yang, Wen ;
Yao, Yongqi ;
Yang, Xin ;
Deng, Yingying ;
Yang, Dingqiao .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (10) :2571-2589
[4]   A NOVEL TRIFLUOROMETHYLATION METHOD OF SATURATED ORGANIC HALIDES [J].
CHEN, QY ;
DUAN, JX .
TETRAHEDRON LETTERS, 1993, 34 (26) :4241-4244
[5]   METHYL FLUOROSULFONYLDIFLUOROACETATE - A NEW TRIFLUOROMETHYLATING AGENT [J].
CHEN, QY ;
WU, SW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (11) :705-706
[6]   Copper-Catalyzed Reductive Trifluoromethylation of Alkyl Iodides with Togni's Reagent [J].
Chen, Yanchi ;
Ma, Guobin ;
Gong, Hegui .
ORGANIC LETTERS, 2018, 20 (15) :4677-4680
[7]   Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds [J].
Cherney, Alan H. ;
Kadunce, Nathaniel T. ;
Reisman, Sarah E. .
CHEMICAL REVIEWS, 2015, 115 (17) :9587-9652
[8]   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
[9]  
d Meijere A., 2014, Metal-Catalyzed Cross-Coupling Reactions and More
[10]  
Denmark S. E., 2014, Metal-Catalyzed Cross-Coup-ling Reactions and More, P475