Categories: C-S Bond Formation >
Synthesis of sulfonyl fluorides
A one-pot Pd-catalyzed reaction of aryl iodides with DABSO and Selectfluor provides aryl sulfonyl fluorides in good yields. Additionally, sulfonyl fluorides can be converted to aryl sulfonamides and sulfonic esters using Cs2CO3 under mild conditions.
A. L. Tribby, I. Rodríguez, S. Shariffudin, N. D. Ball, J. Org. Chem., 2017, 82, 2294-2299.
In a copper-free Sandmeyer-type fluorosulfonylation reaction with Na2S2O5 as the sulfur dioxide source and Selectfluor as fluorine source, aryldiazonium salts are transformed into sulfonyl fluorides. In situ diazotization enables the use of aromatic amines as substrates. The method offers broad functional group tolerance, gram-scale synthesis and late-stage fluorosulfonylation.
T. Zhong, M.-K. Pang, Z.-D. Chen, B. Zhang, J. Weng, G. Lu, Org. Lett., 2020, 22, 2941-2945.
A general and practical copper-catalyzed fluorosulfonylation reaction of a wide range of arenediazonium salts provides arenesulfonyl fluorides using the 1,4-diazabicyclo[2.2.2]octane-bis(sulfur dioxide) adduct as a convenient sulfonyl source in combination with KHF2.
Y. Liu, D. Yu, Y. Guo, J.-C. Xiao, Q.-Y. Chen, C. Liu, Org. Lett., 2020, 22, 2281-2286.