Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, No. 100, Shih-Chuan first Rd, Sanmin District, Kaohsiung City, 807, Taiwan.
Department of Medical Research, Kaohsiung Medical University Hospital, No.100 Tzyou first Rd, Sanmin District, Kaohsiung City, 807, Taiwan.
Org Lett. 2020 Mar 6;22(5):1955-1960. doi: 10.1021/acs.orglett.0c00304. Epub 2020 Feb 19.
Herein, we reported Lewis acid- or Brønsted acid-promoted intramolecular C(sp)-C(sp) bond cleavage and a novel C(sp)-C(sp) bond-forming cascade reaction to synthesize the acridine motif. The metal-free oxidation of the alkyne motif generated the in situ ketone group extracted via a decarbonylation reaction. The mechanistic studies revealed that the electrophilic -iodo species triggered key decarbonylation reactions via consecutive dearomatization/aromatization reactions. In addition, we exploited this acid-promoted C-C bond activation system with internal alkynes to synthesize bis(heteroaryl) ketones.
在此，我们报道了路易斯酸或布朗斯台德酸促进的分子内 C(sp)-C(sp)键断裂和新型 C(sp)-C(sp)键形成级联反应，以合成吖啶基序。炔基序的无金属氧化通过脱羰反应产生了原位酮基。机理研究表明，亲电 -碘物种通过连续的去芳构化/芳构化反应引发关键的脱羰反应。此外，我们利用该酸促进的 C-C 键活化体系与内部炔烃合成了双（杂芳基）酮。
