Synthesis of alkynyl sulfones
A highly efficient, metal-free, and generally applicable iodine-catalyzed reaction of arylacetylenic acids and arylacetylenes with sodium sulfinates provides arylacetylenic sulfones.
J. Meesin, P. Katrun, C. Pareseecharoen, M. Pohmakotr, V. Reutrakul, D. Soorukram, C. Kuhakarn, J. Org. Chem., 2016, 81, 2744-2752.
An electrochemical sulfonylation of alkynes with sodium sulfinates occurs efficiently under transition-metal-free, external oxidant-free, and base-free conditions at room temperature and furnishes diverse alkynyl sulfones in satisfactory yield with broad functional group tolerance.
X. Meng, H. Xu, X. Cao, X.-M. Cai, J. Luo, F. Wang, S. Huang, Org. Lett., 2020, 22, 6827-6831.
The cerium(IV) ammonium nitrate (CAN) mediated reaction of aryl sulfinates and sodium iodide with alkenes afforded vinyl sulfones in very good yields. Alkynes underwent a similar reaction to give β-iodovinyl sulfones, which on treatment with potassium carbonate afforded the corresponding acetylenic sulfones in high yields.
V. Nair, A. Augustine, T. D. Suja, Synthesis, 2002, 2259-2265.