Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products

doi:10.1021/acscatal.0c05372

	Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products
	Xu, Hui 3; Ma, Biao 3; Fu, Zunyun 1; Li, Han-Yuan 3; Wang, Xing 3; Wang, Zhen-Yu 1; Li, Ling-Jun 3; Cheng, Tai-Jin 3; Zheng, Mingyue 2; Dai, Hui-Xiong 3
刊名	ACS CATALYSIS
	2021-02-05
卷号	11 期号:3 页码:1758-1764
关键词	alkynylation Ar-C(O) cleavage ligand palladium late-stage diversification
ISSN号	2155-5435
DOI	10.1021/acscatal.0c05372
通讯作者	Zheng, Mingyue(myzheng@simm.ac.cn) ; Dai, Hui-Xiong(hxdai@simm.ac.cn)
英文摘要	Conversion of the numerous aryl ketones into aryl electrophiles via Ar-C(O) cleavage remains a challenging yet highly desirable transformation in Sonogashira-type coupling. Herein, we report a palladium-catalyzed ligand-promoted alkynylation of unstrained aryl ketones. The protocol allows the alkynylation to be carried out in a one-pot procedure with broad functional-group tolerance and substrate scope. The potential applications of this protocol in drug discovery and chemical biology are further demonstrated by late-stage diversification of a number of pharmaceuticals and natural products. More importantly, two different biologically important fragments derived from a pharmaceutical and natural product could be connected by the consecutive alkynylation of ketones. Distinct from aryl halides in conventional Sonogashira reactions, the protocol provides a practical tool for the 1,2-bifunctionalization of aryl ketone by merging ketone-directed ortho-C-H activation with ligand-promoted ipso-Ar-C(O) alkynylation.
资助项目	Shanghai Institute of Materia Medica ; Chinese Academy of Sciences ; NSFC[21772211] ; NSFC[21920102003] ; Youth Innovation Promotion Association CAS[2014229] ; Youth Innovation Promotion Association CAS[2018293] ; Science and Technology Commission of Shanghai Municipality[17JC1405000] ; Science and Technology Commission of Shanghai Municipality[18431907100] ; Program of Shanghai Academic Research Leader[19XD1424600] ; National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002-006]
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000618540300056
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/295671]
专题	中国科学院上海药物研究所
通讯作者	Zheng, Mingyue; Dai, Hui-Xiong
作者单位	1.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Jiangsu, Peoples R China 2.Chinese Acad Sci, Drug Discovery & Design Ctr, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 3.Univ Chinese Acad Sci, Chinese Acad Sci, Shanghai Inst Mat Medicah, Key Lab Receptor Researc, Shanghai 201203, Peoples R China
推荐引用方式 GB/T 7714	Xu, Hui,Ma, Biao,Fu, Zunyun,et al. Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products[J]. ACS CATALYSIS,2021,11(3):1758-1764.
APA	Xu, Hui.,Ma, Biao.,Fu, Zunyun.,Li, Han-Yuan.,Wang, Xing.,...&Dai, Hui-Xiong.(2021).Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products.ACS CATALYSIS,11(3),1758-1764.
MLA	Xu, Hui,et al."Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products".ACS CATALYSIS 11.3(2021):1758-1764.