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Updated: Sep 16, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Ag(I)/K2S2O8-Mediated Selective Oxidation of Ynamide-Yne via Structural Reshuffling and Consecutive N-Desulfonylation
Mohana Reddy Mutra1, T L Chandana1, Tzu-Pin Wang1
1Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, No. 100, Shiquan first Rd, San-min District, Kaohsiung City 807, Taiwan.
Abstract:
Herein, we developed an intramolecular Ag(I)/K2S2O8-mediated selective oxidation of alkyne in the ynamide-yne framework. Through structural reshuffling and consecutive N-desulfonylation, this process produces multisubstituted indoles (1,2-dicarbonyl). The developed intramolecular methodology exhibits remarkable advantages, including regioselective and chemoselective alkyne oxidation, the use of K2S2O8 as an oxidant and oxygen source, multiple bond cleavages (N-C(sp), O-SO3-, N-SO2R), and the formation of multiple new bonds (two C═O, two C(sp2)-C(sp2), and one N-C(sp2)) in a one-pot reaction. Moreover, this protocol is applicable to gram-scale synthesis and enables further synthetic transformations of the products.
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