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In this study, we first explore how both radical polarity matching and substituent effects, when employed synergistically, can be used to effect regio\u2010 and diastereoselective SF\n                    <jats:sub>5<\/jats:sub>\n                    Cl addition across 1,3\u2010disubstituted (\n                    <jats:italic>viz<\/jats:italic>\n                    . 3\u2010aryl\u20101\u2010carbonyl\u2010substituted) bicyclobutanes (BCBs) to access a class of congested \u03b1\u2010SF\n                    <jats:sub>5<\/jats:sub>\n                    \u2010carbonyl\u2010containing tetrasubstituted cyclobutanes (CBs). Synthetic, computational, and structural studies provide insight on the observed selectivity and reveal unusually close intramolecular SF\n                    <jats:sub>5<\/jats:sub>\n                    \u22efC\u2550X (X\u00a0= C, N, or O) contacts in several SF\n                    <jats:sub>5<\/jats:sub>\n                    \u2010CBs by SC\u2010XRD. Beyond accessing compounds of fundamental interest, we describe a complementary telescoped protocol to facilitate isolation of SF\n                    <jats:sub>5<\/jats:sub>\n                    \u2010CBs as alcohols, as well as a fortuitous observation that led to the synthesis of the first suite of SF\n                    <jats:sub>5<\/jats:sub>\n                    \u2010substituted oxa[2.1.1]bicyclohexanes (OBHs). Finally, we examine the compatibility of SF\n                    <jats:sub>5<\/jats:sub>\n                    \u2010CBs and SF\n                    <jats:sub>5<\/jats:sub>\n                    \u2010OBHs with various reaction conditions to expand the scope of accessible building blocks and report the synthesis of an SF\n                    <jats:sub>5<\/jats:sub>\n                    \u2010OBH\u2010containing drug derivative. Results from comparative in vitro ADME profiling indicate the SF\n                    <jats:sub>5<\/jats:sub>\n                    \u2010OBH motif may serve as an attractive \u201chybrid bioisostere\u201d for the\n                    <jats:italic>meta<\/jats:italic>\n                    \u2010CF\n                    <jats:sub>3<\/jats:sub>\n                    \u2010Ph motif.\n                  <\/jats:p>","DOI":"10.1002\/anie.4256865","type":"journal-article","created":{"date-parts":[[2026,7,7]],"date-time":"2026-07-07T15:08:08Z","timestamp":1783436888000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Strain\u2010Release Pentafluorosulfanylation of Carbonyl\u2010Containing Disubstituted Bicyclobutanes: A Fortuitous Path to SF\n                    <sub>5<\/sub>\n                    \u2010Containing Oxa[2.1.1]bicyclohexanes"],"prefix":"10.1002","volume":"65","author":[{"given":"Alexander M.","family":"Stephens","sequence":"first","affiliation":[{"name":"Department of Chemistry University of California, Davis  Davis California USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jake Anthony","family":"Olvera","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California, Davis  Davis California USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yannick","family":"Kraemer","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California, Davis  Davis California USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tyson","family":"Vu","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California, Davis  Davis California USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wang\u2010Yeuk","family":"Kong","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California, Davis  Davis California USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sudiksha","family":"Chaturvedi","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California, Davis  Davis California USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jeffrey M.","family":"Wang","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California, Davis  Davis California USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lauren M.","family":"Holder","sequence":"additional","affiliation":[{"name":"Novartis BioMedical Research  Emeryville California USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2992-8844","authenticated-orcid":false,"given":"Dean J.","family":"Tantillo","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California, Davis  Davis California USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1047-8924","authenticated-orcid":false,"given":"Cody Ross","family":"Pitts","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California, Davis  Davis California USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,7,7]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b02155"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c00648"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202211892"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202303585"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200301023"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm401375q"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.5b00258"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm501853m"},{"key":"e_1_2_7_10_1","unstructured":"C. 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