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Thus, the reversal of the regioselectivity of the addition reaction of <jats:italic>gem<\/jats:italic>\u2010difluoroalkenes remains a formidable challenge. Herein, we described an unprecedented reversal of regioselectivity of hydrogen atom transfer (HAT) to <jats:italic>gem<\/jats:italic>\u2010difluoroalkenes triggered by Fe\u2212H species for the formation of difluoroalkyl radicals. Hydrogenation of the in situ generated radicals gave difluoromethylated products. Mechanism experiments and theoretical studies revealed that the kinetic effect of the irreversible HAT process resulted in the reversal of the regioselectivity of this scenario, leading to the formation of a less stable <jats:italic>\u03b1<\/jats:italic>\u2010difluoroalkyl radical regioisomer. On basis of this new reaction of <jats:italic>gem<\/jats:italic>\u2010difluoroalkene, the iron\u2010promoted hydrohalogenation of <jats:italic>gem<\/jats:italic>\u2010difluoroalkenes for the efficient synthesis of aliphatic chlorodifluoromethyl\u2010, bromodifluoromethyl\u2010 and iododifluoromethyl\u2010containing compounds was developed. Particularly, this novel hydrohalogenation of <jats:italic>gem<\/jats:italic>\u2010difluoroalkenes provided an effect and large\u2010scale access to various iododifluoromethylated compounds of high value for synthetic application.<\/jats:p>","DOI":"10.1002\/anie.202406324","type":"journal-article","created":{"date-parts":[[2024,4,19]],"date-time":"2024-04-19T02:25:36Z","timestamp":1713493536000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":29,"title":["Reversal of the Regioselectivity of Iron\u2010Promoted Hydrogenation and Hydrohalogenation of <i>gem<\/i>\u2010Difluoroalkenes"],"prefix":"10.1002","volume":"63","author":[{"given":"Yu\u2010Yang","family":"Zhang","sequence":"first","affiliation":[{"name":"Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Science Chinese Academy of Science  345 Lingling Road Shanghai 200032 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuchen","family":"Zhang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Science Chinese Academy of Science  345 Lingling Road Shanghai 200032 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiao\u2010Song","family":"Xue","sequence":"additional","affiliation":[{"name":"Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Science Chinese Academy of Science  345 Lingling Road Shanghai 200032 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7082-756X","authenticated-orcid":false,"given":"Feng\u2010Ling","family":"Qing","sequence":"additional","affiliation":[{"name":"Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Science Chinese Academy of Science  345 Lingling Road Shanghai 200032 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,5,16]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"For recent reviews see:"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.7b01788"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.9b01877"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202003135"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2014.06.014"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cs00221f"},{"key":"e_1_2_7_7_1","unstructured":"For recent reviews 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see:"},{"key":"e_1_2_7_133_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201501475"},{"key":"e_1_2_7_134_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.8b00230"},{"key":"e_1_2_7_135_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202209143"},{"key":"e_1_2_7_136_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c06149"},{"key":"e_1_2_7_137_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.3c00860"},{"key":"e_1_2_7_138_1","unstructured":"\u00a0"},{"key":"e_1_2_7_139_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19990816)38:16<2433::AID-ANIE2433>3.0.CO;2-D"},{"key":"e_1_2_7_140_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)01479-3"},{"key":"e_1_2_7_141_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00476-2"},{"key":"e_1_2_7_142_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg0300275"},{"key":"e_1_2_7_143_1","unstructured":"\u00a0"},{"key":"e_1_2_7_144_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01106a618"},{"key":"e_1_2_7_145_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2005.10.006"},{"key":"e_1_2_7_146_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2010.06.013"},{"key":"e_1_2_7_147_1","unstructured":"For 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see:"},{"key":"e_1_2_7_154_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo9900937"},{"key":"e_1_2_7_155_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC05905E"},{"key":"e_1_2_7_156_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.202101139"},{"key":"e_1_2_7_157_2","doi-asserted-by":"publisher","DOI":"10.1039\/D3SC00027C"},{"key":"e_1_2_7_158_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5OB01302J"},{"key":"e_1_2_7_159_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-1139(96)03510-5"},{"key":"e_1_2_7_160_1","unstructured":"\u00a0"},{"key":"e_1_2_7_161_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol400122k"},{"key":"e_1_2_7_162_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol501674n"},{"key":"e_1_2_7_163_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC09115C"},{"key":"e_1_2_7_164_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c01677"},{"key":"e_1_2_7_165_1","unstructured":"\u00a0"},{"key":"e_1_2_7_166_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201000435"},{"key":"e_1_2_7_167_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja301601b"},{"key":"e_1_2_7_168_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b01258"},{"key":"e_1_2_7_169_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201811346"},{"key":"e_1_2_7_170_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c01941"},{"key":"e_1_2_7_171_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1997-1184"},{"key":"e_1_2_7_172_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c03498"},{"key":"e_1_2_7_173_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc47219a"}],"container-title":["Angewandte 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