Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and their Derivatives

Bedford, C. T.

doi:10.1002/9781119125082.ch2

Cited by 2 publications

(2 citation statements)

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“…Their "textbook" application is related to the synthesis of sulfonamides, which are a classical chemotype in drug discovery. [1,2] Sulfonyl chlorides are commonly used for this purpose due to the optimal combination of high chemical reactivity and synthetic/ commercial accessibility. Sulfonyl fluorides have received much less attention until the last decade when Sharpless proposed sulfur (VI) fluoride exchange (SuFEx) as a highly promising click reaction.…”

Section: Introductionmentioning

confidence: 99%

“…Sulfonyl halides are one of the most important classes of reactants in various areas of chemistry. Their “textbook” application is related to the synthesis of sulfonamides, which are a classical chemotype in drug discovery [1,2] . Sulfonyl chlorides are commonly used for this purpose due to the optimal combination of high chemical reactivity and synthetic/commercial accessibility.…”

Section: Introductionmentioning

confidence: 99%

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Chemoselective Reactions of Functionalized Sulfonyl Halides

Liashuk,

Andriashvili,

Tolmachev

et al. 2023

The Chemical Record

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Chemoselective transformations of functionalized sulfonyl fluorides and chlorides are surveyed comprehensively. It is shown that sulfonyl fluorides provide an excellent selectivity control in their reactions. Thus, numerous conditions are tolerated by the SO2F group – from amide and ester formation to directed ortho‐lithiation and transition‐metal‐catalyzed cross‐couplings. Meanwhile, sulfur (VI) fluoride exchange (SuFEx) is also compatible with numerous functional groups, thus confirming its title of “another click reaction”. On the contrary, with a few exceptions, most transformations of functionalized sulfonyl chlorides typically occur at the SO2Cl moiety.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%