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This approach was demonstrated by C\u2212S bond formation utilizing commercially abundant (hetero)aryl iodides and boronic acids to provide sulfilimine intermediates that undergo thermal elimination of styrene. In contrast, all prior approaches to <jats:italic>N<\/jats:italic>\u2010acylsulfenamides rely on thiol inputs to introduce sulfenamide <jats:italic>S<\/jats:italic>\u2010substituents. A broad scope of reaction inputs was demonstrated including for approved drugs and drug precursors with dense display of functionality. Several different types of sulfur functionalization were performed on a sulfenamide derived from a complex precursor of the blockbuster anticoagulant drug apixaban, highlighting the utility of this approach for the introduction of high oxidation state sulfur groups in complex bioactive compounds. Mechanistic studies established that the key styrene elimination step proceeds by a concerted elimination that does not require reagents or catalysts, and therefore, this one\u2010pot approach should be applicable to the synthesis of <jats:italic>N<\/jats:italic>\u2010acylsulfenamides utilizing diverse electrophiles and reaction conditions for C\u2212S bond formation.<\/jats:p>","DOI":"10.1002\/anie.202315701","type":"journal-article","created":{"date-parts":[[2023,11,28]],"date-time":"2023-11-28T19:02:21Z","timestamp":1701198141000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":29,"title":["Synthesis of <i>N<\/i>\u2010Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One\u2010Pot Sulfur\u2010Arylation and Dealkylation"],"prefix":"10.1002","volume":"63","author":[{"given":"Nathaniel S.","family":"Greenwood","sequence":"first","affiliation":[{"name":"Department of Chemistry Yale University  225 Prospect St. New 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