137668-96-3Relevant academic research and scientific papers
Synthesis of Flavone Derivatives through Versatile Palladium-Catalyzed Cross-Coupling Reactions of Tosyloxy- and Mesyloxyflavones
Yuen, On Ying,Pang, Wai Hang,Chen, Xiangmeng,Chen, Zicong,Kwong, Fuk Yee,So, Chau Ming
, p. 731 - 737 (2019)
Tosyloxy- and mesyloxyflavones derived from abundant and biologically important hydroxyflavones were used to synthesize a series of functionalized flavones through versatile palladium-catalyzed cross-coupling reactions. A Pd(OAc) 2 /2-[2-(dicyclohexylphosphino)phenyl]-1-methyl-1 H -indole system effectively catalyzed the reactions of a broad range of tosyloxy- and mesyloxyflavones as electrophilic coupling partners with various nucleophiles to give the corresponding products in good to excellent yields. Catalyst loadings of as little as 0.1 mol% Pd were successfully used. Importantly, we demonstrated that this protocol provided a significantly improved efficiency in the synthesis of a potential chromen-4-one-based analogue of a potent inhibitor of DNA-dependent protein kinase.
The Regioselective Cleavage of Aryl Tosylates by Electrochemical Reduction
Civitello, Edgar R.,Rapoport, Henry
, p. 834 - 840 (2007/10/02)
The electrochemical reductions of eight bis(tosyloxy)benzenoid compounds were studied as a method for the regioselective cleavage of aryl tosylates.For the methyl bis(tosyloxy)benzoate isomers, a strong preference was observed for cleavage of the tosyl group in conjugation with the electron-withdrawing ester moiety.Thus it was possible to selectively cleave tosyl groups to the ortho or para positions over tosyl groups at the meta positions.The bis(tosyloxy)anisole isomers displayed the opposite regioselectivity favoring cleavage of tosyl groups that were meta to the electron-donating methoxy substituent.The general electrochemical process for the reduction of aryl tosylates has been shown to be selective, high yielding, and reproducible on gram quantities.
