Ruthenium(II)-enabled para-selective C-H difluoromethylation of anilides and their derivatives

doi:10.1038/s41467-018-03341-6

QIBEBT-IR

	Ruthenium(II)-enabled para-selective C-H difluoromethylation of anilides and their derivatives
	Yuan, Chunchen 1; Zhu, Lei 2; Chen, Changpeng 1; Chen, Xiaolan 1; Yang, Yong 3; Lan, Yu 2; Zhao, Yingsheng 1
	2018-03-22
Source Publication	NATURE COMMUNICATIONS
ISSN	2041-1723
Volume	9
Abstract	Transition-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.
Subtype	Article
WOS Headings	Science & Technology
DOI	10.1038/s41467-018-03341-6
WOS Keyword	ORTHO-METALATION STRATEGY ; CARBON-HYDROGEN BONDS ; DIRECT ARYLATION ; BENZENE-DERIVATIVES ; FUNCTIONALIZATION ; ARENES ; ACTIVATION ; ALKYLATION ; FLUORINE ; BROMINATION
Indexed By	SCI
Language	英语
WOS Research Area	Science & Technology - Other Topics
Funding Organization	Natural Science Foundation of China(21772139 ; project of scientific and technologic infrastructure of Suzhou(SZS201708) ; PAPD Project ; 21572149 ; 21772020 ; 21372266)
WOS Subject	Multidisciplinary Sciences
WOS ID	WOS:000428039500007
Publisher	NATURE PUBLISHING GROUP
Citation statistics
Document Type	期刊论文
Identifier	http://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 Author	Lan, Yu; Zhao, Yingsheng
Affiliation	1.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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