Categories: C-S Bond Formation >
Synthesis of sulfonyl fluorides
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Recent Literature
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.
An organobismuth(III) complex bearing a bis-aryl sulfone ligand backbone
catalyzes a synthesis of sulfonyl fluorides from the corresponding (hetero)aryl
boronic acids in the presence of SO2 and Selectfluor. The catalytic protocol
affords excellent yields for a wide range of aryl and heteroaryl boronic acids,
displaying a wide functional group tolerance.
M. Magre, J. Cornella, J. Am. Chem. Soc.,
2021, 143, 21497-21502.
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.
A practical electrochemically method for fluorosulfonylation of both aryl and
alkyl thianthrenium salts works without external redox reagents or metal
catalysts. In combination with C-H thianthrenation of aromatics, this method
provides an interesting tool for the site-selective fluorosulfonylation of
drugs.
X. Kong, Y. Chen, Q. Liu, W. Wang, S. Zhang, Q. Zhang, X. Chen, Y.-Q. Xu, Z.-Y.
Cao, Org. Lett., 2023, 25,
581-586.
An electroreductive protocol for the radical fluorosulfonylation of vinyl
triflates with FSO2Cl as the fluorosulfonyl radical source uses
inexpensive graphite felt as electrodes, thus avoiding the use of a sacrificial
anode. This metal-free protocol offers mild conditions, easy scalability and
provides valuable β-keto sulfonyl fluorides from readily available precursors.
Q. Feng, Y. Fu, Y. Zheng, S. Liao, S. Huang, Org. Lett.,
2022, 24, 3702-3706.
Related
The use of (E)-2-methoxyethene-1-sulfonyl fluoride as sulfonyl fluoride reagent enables a highly atom-economical construction of
enaminyl sulfonyl fluorides under mild and environmentally benign conditions
with MeOH as the sole byproduct.
