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This C\u2212S bond\u2010forming reaction is catalyzed by a readily available small\u2010ring phosphine (phosphetane) in conjunction with a hydrosilane terminal reductant to afford a general entry to sulfenyl electrophiles, including valuable trifluoromethyl, perfluoroalkyl, and heteroaryl derivatives that are otherwise difficult to access. Mechanistic investigations indicate that the twofold deoxygenation of the sulfonyl substrate proceeds by the intervention of an off\u2010cycle resting state thiophosphonium ion. The catalytic method represents an operationally simple protocol using a stable phosphine oxide as a precatalyst and exhibits broad functional\u2010group tolerance.<\/jats:p>","DOI":"10.1002\/anie.201813919","type":"journal-article","created":{"date-parts":[[2019,1,11]],"date-time":"2019-01-11T11:32:42Z","timestamp":1547206362000},"page":"2864-2869","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":101,"title":["Organophosphorus\u2010Catalyzed Deoxygenation of Sulfonyl Chlorides: Electrophilic (Fluoroalkyl)sulfenylation by P<sup>III<\/sup>\/P<sup>V<\/sup>=O Redox Cycling"],"prefix":"10.1002","volume":"58","author":[{"given":"Avipsa","family":"Ghosh","sequence":"first","affiliation":[{"name":"Department of Chemistry Massachusetts Institute of Technology  Cambridge MA 02139 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Morgan","family":"Lecomte","sequence":"additional","affiliation":[{"name":"Department of Chemistry Massachusetts Institute of Technology  Cambridge MA 02139 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shin\u2010Ho","family":"Kim\u2010Lee","sequence":"additional","affiliation":[{"name":"Department of Chemistry Massachusetts Institute of Technology  Cambridge MA 02139 USA"},{"name":"Departamento de Qu\u00edmica Org\u00e1nica Facultad de Ciencias Universidad Aut\u00f3noma de Madrid (UAM)  Cantoblanco 28049 Madrid Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5373-7343","authenticated-orcid":false,"given":"Alexander T.","family":"Radosevich","sequence":"additional","affiliation":[{"name":"Department of Chemistry Massachusetts Institute of Technology  Cambridge MA 02139 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2019,1,25]]},"reference":[{"key":"e_1_2_2_1_1","volume-title":"Organic Sulfur Chemistry","author":"Oae S.","year":"1991"},{"key":"e_1_2_2_2_1","unstructured":"For general reviews on catalyzed oxygen-atom transfer see:"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00082a005"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00019a012"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar980009u"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar700027f"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2013.05.010"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.150747"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00167"},{"key":"e_1_2_2_10_1","unstructured":"\u00a0"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00338a030"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1996-5413"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199526401"},{"key":"e_1_2_2_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19951072317"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)00590-1"},{"key":"e_1_2_2_15_2","first-page":"1","volume-title":"Organosulfur Chemistry in Asymmetric Synthesis","author":"Kagan H. 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