What is it about?
Herein, we reported Lewis acid- or Brønsted acid-promoted intramolecular C(sp2)-C(sp2) bond cleavage and a novel C(sp2)-C(sp2) 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 N-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.
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Why is it important?
transition metal-free unstrained decarbonylation
Perspectives
we reported Lewis acid- or Brønsted acid-promoted intramolecular C(sp2)-C(sp2) bond cleavage and a novel C(sp2)-C(sp2) 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 N-iodo species triggered key decarbonylation reactions via consecutive dearomatization/aromatization reactions. I
Dr Ganesh kumar Dhandabani
National Taiwan University
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This page is a summary of: Acid-Promoted Intramolecular Decarbonylative Coupling Reactions of Unstrained Ketones: A Modular Approach to Synthesis of Acridines and Diaryl Ketones, Organic Letters, February 2020, American Chemical Society (ACS),
DOI: 10.1021/acs.orglett.0c00304.
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