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Their enhanced bioavailability contributes to the widespread presence of this motif in a variety of bioactive compounds. Despite the development of multiple synthetic strategies, a direct method for transferring CF\n                    <jats:sub>3<\/jats:sub>\n                    \u2010containing small rings from their most abundant carboxylic acid surrogates remains a significant challenge. In this work, we overcome the challenging decarboxylation of CF\n                    <jats:sub>3<\/jats:sub>\n                    \u2010cyclopropyl and CF\n                    <jats:sub>3<\/jats:sub>\n                    \u2010cyclobutyl carboxylic acids while leveraging the ligand\u2010to\u2010metal charge transfer (LMCT) excited state of photochemically activated iron complexes. The resulting radicals were then engaged in radical addition to alkenes, followed by a timely hydrogen atom transfer (HAT) process mediated by a thiol donor. This efficient iron\u2010thiol cooperative catalysis enables, for the first time, facile hydroalkylation of alkenes with highly reactive CF\n                    <jats:sub>3<\/jats:sub>\n                    \u2010containing cyclopropyl and cyclobutyl radicals. Synergistic experimental, spectroscopic, and density functional theory (DFT) studies support the proposed reaction mechanism. Additionally, we employed the radical stabilization energy (RSE) scale, developed using isodesmic equations computed at the DFT level, aiming to provide a better understanding of the reluctant radical decarboxylation of small\u2010strained cycloalkanes.\n                  <\/jats:p>","DOI":"10.1002\/anie.202508377","type":"journal-article","created":{"date-parts":[[2025,6,24]],"date-time":"2025-06-24T22:49:45Z","timestamp":1750805385000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Overcoming Challenges in Small\u2010Ring Transfer: Direct Decarboxylative Hydroalkylation of Alkenes via Iron\u2010Thiol Catalysis"],"prefix":"10.1002","volume":"64","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3110-2125","authenticated-orcid":false,"given":"Rahul","family":"Giri","sequence":"first","affiliation":[{"name":"Department of Chemistry, Biochemistry and Pharmaceutical Sciences University of Bern  Freiestrasse 3 Bern 3012 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Po\u2010Kai","family":"Peng","sequence":"additional","affiliation":[{"name":"Department of Chemistry Rice University  6100 Main St Houston Texas 77005 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anthony J.","family":"Fernandes","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Biochemistry and Pharmaceutical Sciences University of Bern  Freiestrasse 3 Bern 3012 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shijin","family":"Yu","sequence":"additional","affiliation":[{"name":"Department of Chemistry Rice University  6100 Main St Houston Texas 77005 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3715-7883","authenticated-orcid":false,"given":"Julian G.","family":"West","sequence":"additional","affiliation":[{"name":"Department of Chemistry Rice University  6100 Main St Houston Texas 77005 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0131-1188","authenticated-orcid":false,"given":"Dmitry","family":"Katayev","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Biochemistry and Pharmaceutical Sciences University of Bern  Freiestrasse 3 Bern 3012 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,7,7]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197908093"},{"key":"e_1_2_8_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19790911104"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja036309a"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.1700271"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/ml400045j"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201402502"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0MD00370K"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.3c00765"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.7b01236"},{"key":"e_1_2_8_9_1","unstructured":"L. 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