1027100-41-9Relevant articles and documents
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.
Block modification of rod-shaped π conjugated carbon frameworks with donor and acceptor groups toward highly fluorescent molecules: Synthesis and emission characteristics
Ochi, Takanori,Yamaguchi, Yoshihiro,Wakamiya, Tateaki,Matsubara, Yoshio,Yoshida, Zen-Ichi
experimental part, p. 1222 - 1231 (2008/10/09)
To create organic molecules that are highly fluorescent at a longer wavelength region, we investigated the synthesis (using Pd-catalyzed cross-coupling) and photophysical properties (Φ f, λ em, τ , λ abs, and ε ) of the following π conjugated molecular rods consisting of p-phenyleneethynylene units modified by donor (OMe) and/or acceptor (CN) groups: (1) side-donor modification systems (SD systems), (2) side-acceptor modification systems (SA systems), and (3) systems consisting of a donor block and an acceptor block (BL systems). As a consequence, very high Φ f values (>0.95) were obtained for BL systems. Bathochromic shifts of λ em for the same π conjugation length were largest for BL systems. Thus we succeeded in creating highly efficient light emitters at a longer wavelength region by block modification (e.g., Φ f = 0.97, λ em = 464 nm for BL-9). Considerably intense solid emission (Φ f ~ 0.5) at a longer wavelength region (500- 560 nm) was also found for BL systems. It has been found that BL-6 and BL-8 exhibit interesting two photon absorption characteristics. This journal is The Royal Society of Chemistry.