17188-67-9Relevant academic research and scientific papers
C?C bond acylation of oxime ethers via NHC catalysis
Yang, Hai-Bin,Wan, Dan-Hong
supporting information, p. 1049 - 1053 (2021/02/01)
An N-heterocyclic carbene (NHC)-catalyzed strategy has been developed to address the issue of using toxic transitional metals in the field of C?C bond activation. The novel reaction mode enables an efficient docking between the cyanoalkyl from the cycloketone oxime derivative and the acyl group from the aldehyde, affording ketonitrile in moderate to good yields, which is one kind of useful building block for synthesizing nitrogen-containing pharmacophores.
Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products
Xu, Hui,Ma, Biao,Fu, Zunyun,Li, Han-Yuan,Wang, Xing,Wang, Zhen-Yu,Li, Ling-Jun,Cheng, Tai-Jin,Zheng, Mingyue,Dai, Hui-Xiong
, p. 1758 - 1764 (2021/02/09)
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.
