QIBEBT-IR
Ruthenium(II)-enabled para-selective C-H difluoromethylation of anilides and their derivatives
Yuan, Chunchen1; Zhu, Lei2; Chen, Changpeng1; Chen, Xiaolan1; Yang, Yong3; Lan, Yu2; Zhao, Yingsheng1
2018-03-22
Source PublicationNATURE COMMUNICATIONS
ISSN2041-1723
Volume9
AbstractTransition-metal-catalyzed direct site-selective functionalization of arene C-H bonds has emerged as an innovative approach for building the core structure of pharmaceutical agents and other versatile complex compounds. However, para-selective C-H functionalization has seldom been explored, only a few examples, such as steric-hindered arenes, electron-rich arenes, and substrates with a directing group, have been reported to date. Here we describe the development of a ruthenium-enabled para-selective C-H difluoromethylation of anilides, indolines, and tetrahydroquinolines. This reaction tolerates various substituted arenes, affording para-difluoromethylation products in moderate to good yields. Results of a preliminary study of the mechanism indicate that chelation-assisted cycloruthenation might play a role in the selective activation of para-CAr-H bonds. Furthermore, this method provides a direct approach for the synthesis of fluorinated drug derivatives, which has important application for drug discovery and development.
SubtypeArticle
WOS HeadingsScience & Technology
DOI10.1038/s41467-018-03341-6
WOS KeywordORTHO-METALATION STRATEGY ; CARBON-HYDROGEN BONDS ; DIRECT ARYLATION ; BENZENE-DERIVATIVES ; FUNCTIONALIZATION ; ARENES ; ACTIVATION ; ALKYLATION ; FLUORINE ; BROMINATION
Indexed BySCI
Language英语
WOS Research AreaScience & Technology - Other Topics
Funding OrganizationNatural Science Foundation of China(21772139 ; project of scientific and technologic infrastructure of Suzhou(SZS201708) ; PAPD Project ; 21572149 ; 21772020 ; 21372266)
WOS SubjectMultidisciplinary Sciences
WOS IDWOS:000428039500007
PublisherNATURE PUBLISHING GROUP
Citation statistics
Document Type期刊论文
Identifierhttp://ir.qibebt.ac.cn/handle/337004/10692
Collection中国科学院青岛生物能源与过程研究所
Corresponding AuthorLan, Yu; Zhao, Yingsheng
Affiliation1.Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
2.Chongqing Univ, Sch Chem & Chem Engn, Chongqing 40030, Peoples R China
3.Chinese Acad Sci, Qingdao Inst Bioenergy & Bioproc Technol, Qingdao 266000, Peoples R China
Recommended Citation
GB/T 7714
Yuan, Chunchen,Zhu, Lei,Chen, Changpeng,et al. Ruthenium(II)-enabled para-selective C-H difluoromethylation of anilides and their derivatives[J]. NATURE COMMUNICATIONS,2018,9.
APA Yuan, Chunchen.,Zhu, Lei.,Chen, Changpeng.,Chen, Xiaolan.,Yang, Yong.,...&Zhao, Yingsheng.(2018).Ruthenium(II)-enabled para-selective C-H difluoromethylation of anilides and their derivatives.NATURE COMMUNICATIONS,9.
MLA Yuan, Chunchen,et al."Ruthenium(II)-enabled para-selective C-H difluoromethylation of anilides and their derivatives".NATURE COMMUNICATIONS 9(2018).
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