{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T12:05:42Z","timestamp":1792497942942,"version":"4.5.0"},"reference-count":48,"publisher":"Wiley","issue":"50","license":[{"start":{"date-parts":[[2019,10,28]],"date-time":"2019-10-28T00:00:00Z","timestamp":1572220800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100007215","name":"Verband der Chemischen Industrie","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100007215","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004189","name":"Max-Planck-Gesellschaft","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004189","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":[[2019,12,9]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Reported here is a simple and practical functionalization of primary sulfonamides, by means of a pyrylium salt (Pyry\u2010BF\n                    <jats:sub>4<\/jats:sub>\n                    ), with nucleophiles. This simple reagent activates the poorly nucleophilic NH\n                    <jats:sub>2<\/jats:sub>\n                    group in a sulfonamide, enabling the formation of one of the best electrophiles in organic synthesis: a sulfonyl chloride. Because of the variety of primary sulfonamides in pharmaceutical contexts, special attention has been focused on the direct conversion of densely functionalized primary sulfonamides by a late\u2010stage formation of the corresponding sulfonyl chloride. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides, sulfonates, sulfides, sulfonyl fluorides, and sulfonic acids. The mild reaction conditions and the high selectivity of Pyry\u2010BF\n                    <jats:sub>4<\/jats:sub>\n                    towards NH\n                    <jats:sub>2<\/jats:sub>\n                    groups permit the formation of sulfonyl chlorides in a late\u2010stage fashion, tolerating a preponderance of sensitive functionalities.\n                  <\/jats:p>","DOI":"10.1002\/anie.201910895","type":"journal-article","created":{"date-parts":[[2019,10,9]],"date-time":"2019-10-09T04:58:21Z","timestamp":1570597101000},"page":"18235-18239","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":75,"title":["Selective Late\u2010Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry\u2010BF\n                    <sub>4<\/sub>"],"prefix":"10.1002","volume":"58","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5127-3445","authenticated-orcid":false,"given":"Alejandro","family":"G\u00f3mez\u2010Palomino","sequence":"first","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  Kaiser-Wilhelm-Platz 1 45470 M\u00fclheim an der Ruhr Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4152-7098","authenticated-orcid":false,"given":"Josep","family":"Cornella","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  Kaiser-Wilhelm-Platz 1 45470 M\u00fclheim an der Ruhr Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2019,10,28]]},"reference":[{"key":"e_1_2_2_1_1","volume-title":"The First Miracle Drugs: How the Sulfa Drugs Transformed Medicine","year":"2006"},{"key":"e_1_2_2_2_1","volume-title":"Drug Discovery: Practices, Processes, and Perspectives","year":"2013"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1007\/s41061-018-0184-5"},{"key":"e_1_2_2_4_1","unstructured":"For selected examples and procedures see:"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja1081124"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b04532"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00093"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309399"},{"key":"e_1_2_2_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201309399"},{"key":"e_1_2_2_9_2","first-page":"101","volume":"27","author":"Flegeau E. F.","year":"2016","journal-title":"Synlett"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201409283"},{"key":"e_1_2_2_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201409283"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0397658"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol201957n"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201700621"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200901510"},{"key":"e_1_2_2_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200901510"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja073872a"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc41249k"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201800699"},{"key":"e_1_2_2_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201800699"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja405949a"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b02266"},{"key":"e_1_2_2_20_1","unstructured":"\u00a0"},{"key":"e_1_2_2_21_2","first-page":"2501","volume":"16","author":"Kim J.-G.","year":"2007","journal-title":"Synlett"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1080\/10426507.2010.488257"},{"key":"e_1_2_2_23_2","first-page":"123","volume-title":"Synthetic Methods in Drug Discovery, Vol.\u20052","author":"Schmitt A.-M. D.","year":"2016"},{"key":"e_1_2_2_24_1","unstructured":"For some examples applied in medicinal chemistry see:"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm800762u"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm800600v"},{"key":"e_1_2_2_27_1","unstructured":"\u00a0"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1339675"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0032-1316890"},{"key":"e_1_2_2_30_1","unstructured":"\u00a0"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1969-34188"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo800424g"},{"key":"e_1_2_2_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201806271"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201806271"},{"key":"e_1_2_2_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b11800"},{"key":"e_1_2_2_35_1","unstructured":"See Supporting Information for details."},{"key":"e_1_2_2_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570270522"},{"key":"e_1_2_2_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB02364A"},{"key":"e_1_2_2_38_1","unstructured":"\u00a0"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja311729d"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/cb5009475"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2018.07.008"},{"key":"e_1_2_2_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462883"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462883"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201910895","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201910895","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.201910895","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201910895","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,8]],"date-time":"2023-09-08T23:38:29Z","timestamp":1694216309000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201910895"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,10,28]]},"references-count":48,"journal-issue":{"issue":"50","published-print":{"date-parts":[[2019,12,9]]}},"alternative-id":["10.1002\/anie.201910895"],"URL":"https:\/\/doi.org\/10.1002\/anie.201910895","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,10,28]]},"assertion":[{"value":"2019-08-26","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-10-28","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}