{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T14:34:16Z","timestamp":1790692456169,"version":"4.1.0"},"reference-count":74,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2015,11,23]],"date-time":"2015-11-23T00:00:00Z","timestamp":1448236800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"Swiss National Science Fundation","award":["200020_137712"],"award-info":[{"award-number":["200020_137712"]}]},{"name":"Swiss National Science Fundation","award":["200020_156989"],"award-info":[{"award-number":["200020_156989"]}]},{"DOI":"10.13039\/501100004240","name":"Academy of Sciences of the Czech Republic","doi-asserted-by":"crossref","award":["61388963"],"award-info":[{"award-number":["61388963"]}],"id":[{"id":"10.13039\/501100004240","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2016,1,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A series of new hypervalent iodine reagents based on the 1,3\u2010dihydro\u20103,3\u2010dimethyl\u20101,2\u2010benziodoxole and 1,2\u2010benziodoxol\u20103\u2010(1<jats:italic>H<\/jats:italic>)\u2010one scaffolds, which contain a functionalized tetrafluoroethyl group, have been prepared, characterized, and used in synthetic applications. Their corresponding electrophilic fluoroalkylation reactions with various sulfur, oxygen, phosphorus, and carbon\u2010centered nucleophiles afford products that feature a tetrafluoroethylene unit, which connects two functional moieties. A related \u03bb<jats:sup>3<\/jats:sup>\u2010iodane that contains a fluorophore was shown to react with a cysteine derivative under mild conditions to give a thiol\u2010tagged product that is stable in the presence of excess thiol. Therefore, these new reagents show a significant potential for applications in chemical biology as tools for fast, irreversible, and selective thiol bioconjugation.<\/jats:p>","DOI":"10.1002\/chem.201503531","type":"journal-article","created":{"date-parts":[[2015,11,23]],"date-time":"2015-11-23T07:39:38Z","timestamp":1448264378000},"page":"417-424","source":"Crossref","is-referenced-by-count":89,"title":["Expanding the Scope of Hypervalent Iodine Reagents for Perfluoroalkylation: From Trifluoromethyl to Functionalized Perfluoroethyl"],"prefix":"10.1002","volume":"22","author":[{"given":"V\u00e1clav","family":"Matou\u0161ek","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ji\u0159\u00ed","family":"V\u00e1clav\u00edk","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter","family":"H\u00e1jek","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Julie","family":"Charpentier","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zs\u00f3fia E.","family":"Blastik","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ewa","family":"Pietrasiak","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alena","family":"Budinsk\u00e1","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Antonio","family":"Togni","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Petr","family":"Beier","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,11,23]]},"reference":[{"key":"e_1_2_5_1_2","first-page":"10","volume-title":"Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications","author":"Kirsch P.","year":"1996"},{"key":"e_1_2_5_2_2","unstructured":"\u00a0"},{"key":"e_1_2_5_3_2","volume-title":"Fluorine in pharmaceutical and medicinal chemistry","year":"2012"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr4002879"},{"key":"e_1_2_5_5_2","unstructured":"\u00a0"},{"key":"e_1_2_5_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2010.03.003"},{"key":"e_1_2_5_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr800221v"},{"key":"e_1_2_5_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr400473a"},{"key":"e_1_2_5_9_2","unstructured":"\u00a0"},{"key":"e_1_2_5_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr941142c"},{"key":"e_1_2_5_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201202624"},{"key":"e_1_2_5_11_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201202624"},{"key":"e_1_2_5_12_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature10647"},{"key":"e_1_2_5_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500223h"},{"key":"e_1_2_5_14_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.6.65"},{"key":"e_1_2_5_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201101535"},{"key":"e_1_2_5_16_2","unstructured":"\u00a0"},{"key":"e_1_2_5_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr1004293"},{"key":"e_1_2_5_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201106668"},{"key":"e_1_2_5_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201106668"},{"key":"e_1_2_5_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo401423h"},{"key":"e_1_2_5_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200501052"},{"key":"e_1_2_5_21_2","unstructured":"\u00a0"},{"key":"e_1_2_5_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc39235j"},{"key":"e_1_2_5_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol400184t"},{"key":"e_1_2_5_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201200140"},{"key":"e_1_2_5_24_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201200140"},{"key":"e_1_2_5_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206556"},{"key":"e_1_2_5_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201206556"},{"key":"e_1_2_5_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201202623"},{"key":"e_1_2_5_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201202623"},{"key":"e_1_2_5_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo502040t"},{"key":"e_1_2_5_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201306082"},{"key":"e_1_2_5_28_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201306082"},{"key":"e_1_2_5_29_2","unstructured":"\u00a0"},{"key":"e_1_2_5_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja5093776"},{"key":"e_1_2_5_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b03587"},{"key":"e_1_2_5_32_2","unstructured":"\u00a0"},{"key":"e_1_2_5_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b01510"},{"key":"e_1_2_5_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2014.08.011"},{"key":"e_1_2_5_35_2","unstructured":"\u00a0"},{"key":"e_1_2_5_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201100667"},{"key":"e_1_2_5_37_2","first-page":"1187","author":"Chernykh Y.","year":"2012","journal-title":"Synlett"},{"key":"e_1_2_5_38_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2014.10.019"},{"key":"e_1_2_5_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2014.08.004"},{"key":"e_1_2_5_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2013.07.012"},{"key":"e_1_2_5_41_2","unstructured":"\u00a0"},{"key":"e_1_2_5_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr941149u"},{"key":"e_1_2_5_43_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.60.3307"},{"key":"e_1_2_5_44_2","unstructured":"\u00a0"},{"key":"e_1_2_5_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo701318n"},{"key":"e_1_2_5_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2008.01.008"},{"key":"e_1_2_5_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo400774u"},{"key":"e_1_2_5_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200603497"},{"key":"e_1_2_5_48_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200603497"},{"key":"e_1_2_5_49_2","unstructured":"Double letter numbering of products11was adopted for easy identification of the respective reagents and substrates used for their synthesis."},{"key":"e_1_2_5_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201402225"},{"key":"e_1_2_5_51_2","doi-asserted-by":"publisher","DOI":"10.1039\/b801424h"},{"key":"e_1_2_5_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs300089y"},{"key":"e_1_2_5_53_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc11812a"},{"key":"e_1_2_5_54_2","doi-asserted-by":"publisher","DOI":"10.3987\/COM-12-S(N)101"},{"key":"e_1_2_5_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol2023328"},{"key":"e_1_2_5_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2012.07.134"},{"key":"e_1_2_5_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201406181"},{"key":"e_1_2_5_57_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201406181"},{"key":"e_1_2_5_58_2","unstructured":"\u00a0"},{"key":"e_1_2_5_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200900942"},{"key":"e_1_2_5_59_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200900942"},{"key":"e_1_2_5_60_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2014.09.002"},{"key":"e_1_2_5_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/cb400828a"},{"key":"e_1_2_5_62_2","unstructured":"\u00a0"},{"key":"e_1_2_5_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200890217"},{"key":"e_1_2_5_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/pro.652"},{"key":"e_1_2_5_65_2","volume-title":"Bioconjugation Techniques","author":"Hermanson G. T.","year":"2013"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201503531","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201503531","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201503531","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T14:30:05Z","timestamp":1760279405000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201503531"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,11,23]]},"references-count":74,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2016,1,4]]}},"alternative-id":["10.1002\/chem.201503531"],"URL":"https:\/\/doi.org\/10.1002\/chem.201503531","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,11,23]]}}}