4.7 Article

TFA-Mediated DMSO-Participant Sequential Oxidation/1,3-Dipolar Cycloaddition Cascade of Pyridinium Ylides for the Assembly of Indolizines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 5, Pages 2962-2968

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02755

Keywords

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Funding

  1. National Natural Science Foundation of China [21472056, 21772051, 21801022]
  2. Yangtze Youth Talents Fund [2016cqn25]
  3. Doctoral Scientific Research Startup Foundation of Yangtze University [801090010135]

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A trifluoroacetic acid (TFA)-mediated cascade oxidation/1,3-dipolar cycloaddition reaction of stabilized pyridinium salts with dimethyl sulfoxide (DMSO) has been developed in the presence of K2S2O8 and trimethylethylenediamine (TMEDA). In this transition-metal-free reaction, DMSO acts as a one-carbon source, thus providing a convenient method for the efficient and direct synthesis of various indolizine derivatives.

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