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Compared to Appel\u2010type amidations (PS\u2010PPh<jats:sub>3<\/jats:sub>), the developed \u2018catch\u2010and\u2010release\u2019 approach (PS\u2010HOBt) afforded near\u2010quantitative amide conversions. Utilising this strategy, sulfonyl chloride amenability enabled facile access to an expanded library of sulfonate and sulfonamides. Post\u2010constructional peptide modification was also demonstrated, affording two <jats:italic>N<\/jats:italic><jats:sup>\u03b2<\/jats:sup>\u2010functionalised pentapeptides in high yields and purities. 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