Synthesis of sulfonyl fluorides

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Photoredox catalysis enables a mild and scalable preparation of alkyl sulfonyl fluorides from readily available alkyl bromides and alcohols via halogen atom transfer (XAT), followed by SO₂ capture and fluorination. The mild method has been scaled up to 5 g using a continuous stirred tank reactor cascade.
A. Gutiérrez-González, S. Karlsson, D. Leonori, M. P. Plesniak, Org. Lett., 2024, 26, 3972-3976.

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.

Photoactivation of an electron donor-acceptor (EDA) complex enables a radical hydro-fluorosulfonylation of propargyl alcohols with FSO₂Cl. The reaction does not require photocatalysts, bases, hydrogen donor reagents, any other additives, and harsh conditions, enabling the facile synthesis of various functionalized γ-hydroxy (E)-alkenylsulfonyl fluorides.
Y. Zhang, Q. Feng, Y. Zheng, Y. Lu, S. Liao, S. Huang, Org. Lett., 2024, 26, 1410-1415.

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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.