Transformations of Aryl Ketones via Ligand-Promoted C-C Bond Activation

doi:10.1002/anie.202006740

	Transformations of Aryl Ketones via Ligand-Promoted C-C Bond Activation
	Li, Hanyuan 2; Ma, Biao 2; Liu, Qi-Sheng 2; Wang, Mei-Ling 1; Wang, Zhen-Yu 3; Xu, Hui 2; Li, Ling-Jun 2; Wang, Xing 2; Dai, Hui-Xiong 2
刊名	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
	2020-07-01
页码	7
关键词	aryl ketones borylation C-C bond activation Pd catalysis
ISSN号	1433-7851
DOI	10.1002/anie.202006740
通讯作者	Dai, Hui-Xiong(hxdai@simm.ac.cn)
英文摘要	The coupling of aromatic electrophiles (aryl halides, aryl ethers, aryl acids, aryl nitriles etc.) with nucleophiles is a core methodology for the synthesis of aryl compounds. Transformations of aryl ketones in an analogous manner via carbon-carbon bond activation could greatly expand the toolbox for the synthesis of aryl compounds due to the abundance of aryl ketones. An exploratory study of this approach is typically based on carbon-carbon cleavage triggered by ring-strain release and chelation assistance, and the products are also limited to a specific structural motif. Here we report a ligand-promoted beta-carbon elimination strategy to activate the carbon-carbon bonds, which results in a range of transformations of aryl ketones, leading to useful aryl borates, and also to biaryls, aryl nitriles, and aryl alkenes. The use of a pyridine-oxazoline ligand is crucial for this catalytic transformation. A gram-scale borylation reaction of an aryl ketone via a simple one-pot operation is reported. The potential utility of this strategy is also demonstrated by the late-stage diversification of drug molecules probenecid, adapalene, and desoxyestrone, the fragrance tonalid as well as the natural product apocynin.
资助项目	Shanghai Institute of Materia Medica ; Chinese Academy of Sciences ; NSFC[21772211] ; Youth Innovation Promotion Association CAS[2014229] ; Youth Innovation Promotion Association CAS[2018293] ; Science and Technology Commission of Shanghai Municipality[17JC1405000] ; Program of Shanghai Academic Research Leader[19XD1424600] ; National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002-006]
WOS关键词	CATALYZED DECARBONYLATIVE BORYLATION ; CROSS-COUPLING REACTIONS ; CLEAVAGE ; STRATEGY ; EXCHANGE ; OXIMES ; ETHERS
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000544629400001
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/291941]
专题	中国科学院上海药物研究所
通讯作者	Dai, Hui-Xiong
作者单位	1.Univ Sci & Technol China, Nano Sci & Technol Inst, Suzhou 215123, Jiangsu, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, Shanghai 201203, Peoples R China 3.Nanjing Univ Chinese Med, Sch Pharm, Nanjing 210023, Jiangsu, Peoples R China
推荐引用方式 GB/T 7714	Li, Hanyuan,Ma, Biao,Liu, Qi-Sheng,et al. Transformations of Aryl Ketones via Ligand-Promoted C-C Bond Activation[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2020:7.
APA	Li, Hanyuan.,Ma, Biao.,Liu, Qi-Sheng.,Wang, Mei-Ling.,Wang, Zhen-Yu.,...&Dai, Hui-Xiong.(2020).Transformations of Aryl Ketones via Ligand-Promoted C-C Bond Activation.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,7.
MLA	Li, Hanyuan,et al."Transformations of Aryl Ketones via Ligand-Promoted C-C Bond Activation".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020):7.