{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T01:46:03Z","timestamp":1785894363530,"version":"3.56.0"},"reference-count":225,"publisher":"Wiley","issue":"46","license":[{"start":{"date-parts":[[2022,10,6]],"date-time":"2022-10-06T00:00:00Z","timestamp":1665014400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000009","name":"Foundation for the National Institutes of Health","doi-asserted-by":"publisher","award":["GM-130395"],"award-info":[{"award-number":["GM-130395"]}],"id":[{"id":"10.13039\/100000009","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2022,11,14]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Stereochemically defined organofluorine compounds are vital to drug discovery and many applicable catalytic strategies have been introduced for accessing these entities stereoselectively. One approach entails incorporation of a fluorine atom (C\u2212F bond formation) or an organofluorine moiety (e.g., CF<jats:sub>3<\/jats:sub>or CF<jats:sub>2<\/jats:sub>H), and another exploits commercially available compounds with one or more fluorine atoms. Here, we present the state\u2010of\u2010the\u2010art regarding the use of alkenyl and allylic fluorides in preparation of stereochemically defined fluoro\u2010organic molecules. Allylic and alkenyl fluorides may be purchased or generated from a commercially available acid, carboxylate salt, ester, aldehyde hydrate, or ketone bearing several fluorine atoms next to a carbonyl group. We underscore the untapped potential of purchasable organofluorine compounds, many allylic and alkenyl fluorides, as launching points for development of stereoselective processes that are of value to therapeutic science.<\/jats:p>","DOI":"10.1002\/anie.202208742","type":"journal-article","created":{"date-parts":[[2022,8,26]],"date-time":"2022-08-26T12:08:56Z","timestamp":1661515736000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":43,"title":["Catalytic and Stereoselective Transformations with Easily Accessible and Purchasable Allyl and Alkenyl Fluorides"],"prefix":"10.1002","volume":"61","author":[{"given":"Paulo H. S.","family":"Paioti","sequence":"first","affiliation":[{"name":"Supramolecular Science and Engineering Institute, University of Strasbourg, CNRS 67000 Strasbourg France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stella A.","family":"Gonsales","sequence":"additional","affiliation":[{"name":"Supramolecular Science and Engineering Institute, University of Strasbourg, CNRS 67000 Strasbourg France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shibo","family":"Xu","sequence":"additional","affiliation":[{"name":"Department of Chemistry Merkert Chemistry Center Boston College Chestnut Hill MA 02467 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ali","family":"Nikbakht","sequence":"additional","affiliation":[{"name":"Supramolecular Science and Engineering Institute, University of Strasbourg, CNRS 67000 Strasbourg France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Diana C.","family":"Fager","sequence":"additional","affiliation":[{"name":"Department of Chemistry Merkert Chemistry Center Boston College Chestnut Hill MA 02467 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qinghe","family":"Liu","sequence":"additional","affiliation":[{"name":"Department of Chemistry Merkert Chemistry Center Boston College Chestnut Hill MA 02467 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1470-6456","authenticated-orcid":false,"given":"Amir H.","family":"Hoveyda","sequence":"additional","affiliation":[{"name":"Supramolecular Science and Engineering Institute, University of Strasbourg, CNRS 67000 Strasbourg France"},{"name":"Department of Chemistry Merkert Chemistry Center Boston College Chestnut Hill MA 02467 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,10,6]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"For example see:"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr4002879"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00392"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.7b00226"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB00764C"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.7b01788"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201901840"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.0c00830"},{"key":"e_1_2_3_9_1","unstructured":"\u00a0"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2014.06.014"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.isci.2020.101467"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201402023"},{"key":"e_1_2_3_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0cs00221f"},{"key":"e_1_2_3_14_1","unstructured":"For examples of aldol additions:"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/b900474b"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol2001039"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo2020104"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja302511t"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2016.02.001"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b00828"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC00330G"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2016.12.008"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201700190"},{"key":"e_1_2_3_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201700190"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2018.03.054"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201916129"},{"key":"e_1_2_3_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201916129"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201814607"},{"key":"e_1_2_3_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201814607"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.09.048"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b04039"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b08443"},{"key":"e_1_2_3_30_1","unstructured":"For example see:"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol047431x"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201103240"},{"key":"e_1_2_3_32_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201103240"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature14617"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201607918"},{"key":"e_1_2_3_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201607918"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2816"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b03262"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1718474115"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b02550"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01738"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201910008"},{"key":"e_1_2_3_40_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201910008"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b00622"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202001184"},{"key":"e_1_2_3_42_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202001184"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0OB01725F"},{"key":"e_1_2_3_44_1","unstructured":"\u00a0"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201001546"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500277b"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500706a"},{"key":"e_1_2_3_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00778"},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC05181J"},{"key":"e_1_2_3_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202112251"},{"key":"e_1_2_3_50_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202112251"},{"key":"e_1_2_3_51_1","unstructured":"\u00a0"},{"key":"e_1_2_3_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00736F"},{"key":"e_1_2_3_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.0c00029"},{"key":"e_1_2_3_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.0c00525"},{"key":"e_1_2_3_55_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201201278"},{"key":"e_1_2_3_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201201278"},{"key":"e_1_2_3_56_1","unstructured":"\u00a0"},{"key":"e_1_2_3_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201301123"},{"key":"e_1_2_3_57_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201301123"},{"key":"e_1_2_3_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol502941d"},{"key":"e_1_2_3_59_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b01494"},{"key":"e_1_2_3_60_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201602542"},{"key":"e_1_2_3_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201602542"},{"key":"e_1_2_3_61_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b01498"},{"key":"e_1_2_3_62_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201002065"},{"key":"e_1_2_3_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201002065"},{"key":"e_1_2_3_63_1","unstructured":"\u00a0"},{"key":"e_1_2_3_64_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)01552-5"},{"key":"e_1_2_3_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo015587u"},{"key":"e_1_2_3_66_1","unstructured":"\u00a0"},{"key":"e_1_2_3_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201600989"},{"key":"e_1_2_3_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202207334"},{"key":"e_1_2_3_68_3","doi-asserted-by":"crossref","first-page":"e202207334","DOI":"10.1002\/ange.202207334","volume":"134","year":"2022","journal-title":"Angew. Chem."},{"key":"e_1_2_3_69_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-29464-5"},{"key":"e_1_2_3_70_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01730"},{"key":"e_1_2_3_71_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC01432E"},{"key":"e_1_2_3_72_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b02772"},{"key":"e_1_2_3_73_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c02894"},{"key":"e_1_2_3_74_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201301027"},{"key":"e_1_2_3_75_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA00093B"},{"key":"e_1_2_3_76_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00612"},{"key":"e_1_2_3_77_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b11476"},{"key":"e_1_2_3_78_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC08480F"},{"key":"e_1_2_3_79_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol500157b"},{"key":"e_1_2_3_80_1","unstructured":"\u00a0"},{"key":"e_1_2_3_81_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201402243"},{"key":"e_1_2_3_82_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b02320"},{"key":"e_1_2_3_83_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB00119J"},{"key":"e_1_2_3_84_1","unstructured":"\u00a0"},{"key":"e_1_2_3_85_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0035-1561460"},{"key":"e_1_2_3_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c00336"},{"key":"e_1_2_3_87_1","unstructured":"\u00a0"},{"key":"e_1_2_3_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja400650m"},{"key":"e_1_2_3_89_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4QO00265B"},{"key":"e_1_2_3_90_2","unstructured":"Ref.\u2005[28b]."},{"key":"e_1_2_3_91_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3OB42329H"},{"key":"e_1_2_3_92_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201508371"},{"key":"e_1_2_3_92_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201508371"},{"key":"e_1_2_3_93_1","unstructured":"\u00a0"},{"key":"e_1_2_3_94_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b07573"},{"key":"e_1_2_3_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00089a042"},{"key":"e_1_2_3_96_1","doi-asserted-by":"publisher","DOI":"10.1016\/0957-4166(94)80116-9"},{"key":"e_1_2_3_97_1","unstructured":"For further discussion see:"},{"key":"e_1_2_3_98_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200805604"},{"key":"e_1_2_3_98_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200805604"},{"key":"e_1_2_3_99_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102398"},{"key":"e_1_2_3_99_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201102398"},{"key":"e_1_2_3_100_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b02792"},{"key":"e_1_2_3_101_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201707375"},{"key":"e_1_2_3_101_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201707375"},{"key":"e_1_2_3_102_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202015946"},{"key":"e_1_2_3_102_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202015946"},{"key":"e_1_2_3_103_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202205508"},{"key":"e_1_2_3_103_2","doi-asserted-by":"crossref","first-page":"e202205508","DOI":"10.1002\/ange.202205508","volume":"134","year":"2022","journal-title":"Angew. Chem."},{"key":"e_1_2_3_104_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC05076A"},{"key":"e_1_2_3_105_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201008296"},{"key":"e_1_2_3_105_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201008296"},{"key":"e_1_2_3_106_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b04374"},{"key":"e_1_2_3_107_1","unstructured":"For preparation of the alkenyl acetates see:"},{"key":"e_1_2_3_108_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo400280p"},{"key":"e_1_2_3_109_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c01957"},{"key":"e_1_2_3_110_1","unstructured":"\u00a0"},{"key":"e_1_2_3_111_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja511458k"},{"key":"e_1_2_3_112_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b11064"},{"key":"e_1_2_3_113_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202000109"},{"key":"e_1_2_3_114_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(97)00683-2"},{"key":"e_1_2_3_115_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc17140f"},{"key":"e_1_2_3_116_1","unstructured":"\u00a0"},{"key":"e_1_2_3_117_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1998-1677"},{"key":"e_1_2_3_118_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(99)00005-8"},{"key":"e_1_2_3_119_1","unstructured":"\u00a0"},{"key":"e_1_2_3_120_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2066169"},{"key":"e_1_2_3_121_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201204493"},{"key":"e_1_2_3_122_1","unstructured":"\u00a0"},{"key":"e_1_2_3_123_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob07022g"},{"key":"e_1_2_3_124_2","doi-asserted-by":"publisher","DOI":"10.1002\/cjoc.201090289"},{"key":"e_1_2_3_125_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5QO00407A"},{"key":"e_1_2_3_126_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol200374m"},{"key":"e_1_2_3_127_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b03213"},{"key":"e_1_2_3_128_1","unstructured":"\u00a0"},{"key":"e_1_2_3_129_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c03406"},{"key":"e_1_2_3_130_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c04131"},{"key":"e_1_2_3_131_1","doi-asserted-by":"publisher","DOI":"10.1055\/a-1274-2959"},{"key":"e_1_2_3_132_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b08343"},{"key":"e_1_2_3_133_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202114918"},{"key":"e_1_2_3_133_2","doi-asserted-by":"crossref","first-page":"e202114918","DOI":"10.1002\/ange.202114918","volume":"134","year":"2022","journal-title":"Angew. Chem."},{"key":"e_1_2_3_134_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm1013693"},{"key":"e_1_2_3_135_1","unstructured":"\u00a0"},{"key":"e_1_2_3_136_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC05225A"},{"key":"e_1_2_3_137_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201708224"},{"key":"e_1_2_3_137_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201708224"},{"key":"e_1_2_3_138_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c00518"},{"key":"e_1_2_3_139_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c02331"},{"key":"e_1_2_3_140_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b07844"},{"key":"e_1_2_3_141_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202003755"},{"key":"e_1_2_3_141_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202003755"},{"key":"e_1_2_3_142_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b04902"},{"key":"e_1_2_3_143_1","unstructured":"\u00a0"},{"key":"e_1_2_3_144_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201803663"},{"key":"e_1_2_3_145_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2018.07.003"},{"key":"e_1_2_3_146_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b11382"},{"key":"e_1_2_3_147_1","unstructured":"\u00a0"},{"key":"e_1_2_3_148_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201906283"},{"key":"e_1_2_3_148_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201906283"},{"key":"e_1_2_3_149_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2011.03.007"},{"key":"e_1_2_3_150_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c02321"},{"key":"e_1_2_3_151_1","unstructured":"S. Xu J. del\u2005Pozo F. Romiti Y. Fu B.\u2005K. Mai R.\u2005J. Morrison K. Lee S. Hu M.\u2005J. Koh J. Lee X. Li P. Liu A.\u2005H. Hoveyda doi.org\/10.1038\/s41557-022-01054-4."},{"key":"e_1_2_3_152_1","unstructured":"\u00a0"},{"key":"e_1_2_3_153_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm100863x"},{"key":"e_1_2_3_154_2","doi-asserted-by":"publisher","DOI":"10.1007\/s40265-014-0247-z"},{"key":"e_1_2_3_155_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-020-2399-1"},{"key":"e_1_2_3_156_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100166a"},{"key":"e_1_2_3_157_1","unstructured":"The role of cesium carboxylate is confirmed in two other instances. In one case subjection of a trifluoromethyl-substituted alkene to 10\u2005mol\u2009% of a chiral bisphosphine-Cu\u2212H complex CsOAc and a benzoyloxyamine afforded the desired amine in high enantiomeric purity. It was more recently shown that a trifluoromethyl-substituted alkene may be alkylated when CsOPiv and 18-crown-6 are present. The polyether likely attenuates the cesium cation's ability to interact with the fluoride leaving group an event that would favor Cu\u2212F elimination. See:"},{"key":"e_1_2_3_158_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01471"},{"key":"e_1_2_3_159_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.1c02947"},{"key":"e_1_2_3_160_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2861"},{"key":"e_1_2_3_161_1","doi-asserted-by":"publisher","DOI":"10.1039\/b105031c"},{"key":"e_1_2_3_162_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp206195g"},{"key":"e_1_2_3_163_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature21043"},{"key":"e_1_2_3_164_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b11178"},{"key":"e_1_2_3_165_1","unstructured":"\u00a0"},{"key":"e_1_2_3_166_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)99640-0"},{"key":"e_1_2_3_167_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)91964-6"},{"key":"e_1_2_3_168_1","unstructured":"\u00a0"},{"key":"e_1_2_3_169_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102790"},{"key":"e_1_2_3_169_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201102790"},{"key":"e_1_2_3_170_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol200302h"},{"key":"e_1_2_3_171_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2005.06.035"},{"key":"e_1_2_3_172_1","unstructured":"\u00a0"},{"key":"e_1_2_3_173_2","doi-asserted-by":"publisher","DOI":"10.1039\/b907983a"},{"key":"e_1_2_3_174_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201100495"},{"key":"e_1_2_3_175_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.13.262"},{"key":"e_1_2_3_176_2","doi-asserted-by":"publisher","DOI":"10.1021\/acschemneuro.8b00085"},{"key":"e_1_2_3_177_1","unstructured":"For methods designed for synthesis of trisubstituted alkenyl fluorides see:"},{"key":"e_1_2_3_178_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cs00201a"},{"key":"e_1_2_3_179_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature10108"},{"key":"e_1_2_3_180_2","unstructured":"Ref.\u2005[72];"},{"key":"e_1_2_3_181_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206566"},{"key":"e_1_2_3_181_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201206566"},{"key":"e_1_2_3_182_2","unstructured":"Ref.\u2005[6b];"},{"key":"e_1_2_3_183_2","unstructured":"Ref. [6d];"},{"key":"e_1_2_3_184_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0036-1591867"},{"key":"e_1_2_3_185_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201500597"},{"key":"e_1_2_3_186_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc31743e"},{"key":"e_1_2_3_187_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202002543"},{"key":"e_1_2_3_188_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature17396"},{"key":"e_1_2_3_189_1","unstructured":"\u00a0"},{"key":"e_1_2_3_190_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0715952"},{"key":"e_1_2_3_191_2","doi-asserted-by":"publisher","DOI":"10.1039\/b801687a"},{"key":"e_1_2_3_192_2","doi-asserted-by":"publisher","DOI":"10.1021\/om800463n"},{"key":"e_1_2_3_193_1","unstructured":"\u00a0"},{"key":"e_1_2_3_194_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00385a007"},{"key":"e_1_2_3_195_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja952789x"},{"key":"e_1_2_3_196_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aaf4622"},{"key":"e_1_2_3_197_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202001612"},{"key":"e_1_2_3_198_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-022-00893-5"},{"key":"e_1_2_3_199_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja962780a"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202208742","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202208742","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202208742","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,11,26]],"date-time":"2023-11-26T06:16:07Z","timestamp":1700979367000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202208742"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,10,6]]},"references-count":225,"journal-issue":{"issue":"46","published-print":{"date-parts":[[2022,11,14]]}},"alternative-id":["10.1002\/anie.202208742"],"URL":"https:\/\/doi.org\/10.1002\/anie.202208742","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,10,6]]},"assertion":[{"value":"2022-06-17","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-10-06","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202208742"}}