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Gold‐Catalyzed Oxidation/C−H Functionalization of Ynones: Efficient and Rapid Access to Functionalized Polycyclic Salicyl Ketones
Author(s) -
Ji Kegong,
Yang Fang,
Gao Shiyue,
Tang Jiangjiang,
Gao Jinming
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600736
Subject(s) - ketone , chemistry , diazo , catalysis , combinatorial chemistry , aryl , surface modification , yield (engineering) , organic chemistry , alkyl , materials science , metallurgy
An efficient strategy to construct salicyl ketones through gold‐catalyzed oxidation/C−H functionalization of ynones is reported. A variety of functionalized salicyl ketones are readily accessed by utilizing this non‐diazo approach, thus providing a viable alternative to synthetically useful salicyl ketones with a yield up to 98 %. The α‐oxo gold carbenes generated in situ through gold‐catalyzed oxidation of ynones can be trapped effectively by internal aryl and heteroaromatic groups. Electronic and steric effects were also investigated in this reaction. The anticancer activity of one salicyl ketone analogue was investigated and its cytotoxicity assays against the PC‐3 prostate cancer cell line and SKOV‐3 human ovarian carcinoma cell line yield IC 50 were 0.81±0.05 and 0.87±0.15 μ m , respectively, demonstrating that salicyl ketone analogues showed good anticancer activity.