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Org. Lett. 2024, 26, 5951 − 5955. DOI: 10.1021/acs.orglett.4c01908 ◆ When an arylsulfonyl chloride cannot be
bought in bulk, a flexible alternative to thiol or disulfide oxidation is to
diazotize an aniline feedstock ahead of reaction with a sulfur dioxide
equivalent. ◆ Scientists at Idorsia modified literature
conditions for this reaction to make it more scale-friendly. ◆ By performing an in situ Sandmeyer-like
reaction with 1,4-diazabicyclo[2.2.2]octanebis(sulfur dioxide) (DABSO), the
aryldiazonium salt intermediate formed on dosing in tert-butyl nitrite only
accumulates where it is electron-rich. ◆ The authors demonstrate the procedure to
form a range of electron-poor and electron-rich arylsulfonyl chlorides, and
react it in situ with an excess of morpholine. ◆ One example is described where the
Sandmeyer-like reaction is worked up to allow the isolation of the arylsulfonyl
chloride itself.
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