{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T04:00:38Z","timestamp":1790827238366,"version":"4.1.0"},"reference-count":95,"publisher":"Wiley","issue":"56","license":[{"start":{"date-parts":[[2021,8,26]],"date-time":"2021-08-26T00:00:00Z","timestamp":1629936000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["19H02716"],"award-info":[{"award-number":["19H02716"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["20K05511"],"award-info":[{"award-number":["20K05511"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2021,10,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>1,3\u2010Diamines are an important class of compounds that are broadly found in natural products and are also widely used as building blocks in organic synthesis. Although the intramolecular C\u2212H amination of <jats:italic>N<\/jats:italic>\u2010alkylsulfamide derivatives is a reliable method for the construction of 1,3\u2010diamine structures, the majority of these methods involve the use of a transition\u2010metal catalyst. We herein report on a new transition\u2010metal\u2010free method using <jats:italic>tert<\/jats:italic>\u2010butyl hypoiodite (<jats:italic>t<\/jats:italic>\u2010BuOI) or <jats:italic>N<\/jats:italic>\u2010iodosuccinimide (NIS), enabling secondary non\u2010benzylic and tertiary C\u2212H amination reactions to proceed. The cyclic sulfamide products can be easily transformed into 1,3\u2010diamines. Mechanistic investigations revealed that amination reactions using <jats:italic>t<\/jats:italic>\u2010BuOI or NIS each proceed via different pathways.<\/jats:p>","DOI":"10.1002\/chem.202102635","type":"journal-article","created":{"date-parts":[[2021,8,17]],"date-time":"2021-08-17T09:36:22Z","timestamp":1629192982000},"page":"13971-13976","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Intramolecular C\u2212H Amination of <i>N<\/i>\u2010Alkylsulfamides by <i>tert<\/i>\u2010Butyl Hypoiodite or <i>N<\/i>\u2010Iodosuccinimide"],"prefix":"10.1002","volume":"27","author":[{"given":"Kensuke","family":"Kiyokawa","sequence":"first","affiliation":[{"name":"Department of Applied Chemistry Graduate School of Engineering Osaka University  Yamadaoka 2\u20131 Suita Osaka 565-0871 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Keisuke","family":"Jou","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Graduate School of Engineering Osaka University  Yamadaoka 2\u20131 Suita Osaka 565-0871 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Satoshi","family":"Minakata","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Graduate School of Engineering Osaka University  Yamadaoka 2\u20131 Suita Osaka 565-0871 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,8,26]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr0404085"},{"key":"e_1_2_2_2_1","unstructured":"\u00a0"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar7000233"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr040107v"},{"key":"e_1_2_2_5_1","unstructured":"For 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These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."},{"key":"e_1_2_2_72_1","unstructured":"In the1H NMR spectrum of the mixture signals corresponding to remainingt-BuOI were not observed which is probably in equilibrium witht-BuOH in the mixture."},{"key":"e_1_2_2_73_1","unstructured":"The reaction was performed on the benchtop in the presence of a fluorescent light on the ceiling."},{"key":"e_1_2_2_74_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC07164C"},{"key":"e_1_2_2_75_1","unstructured":"See the Supporting Information for details."},{"key":"e_1_2_2_76_1","unstructured":"For examples ofN N-diiodosulfonamides see:"},{"key":"e_1_2_2_77_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201201680"},{"key":"e_1_2_2_78_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo1015213"},{"key":"e_1_2_2_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol402276f"},{"key":"e_1_2_2_80_1","unstructured":"A substitution through a halogen bonding activation may be possible."},{"key":"e_1_2_2_81_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00081"},{"key":"e_1_2_2_82_1","unstructured":"Although the mixture of1\u2009vwith two equimolar amounts of NIS in MeNO2was monitored by UV-Vis spectrophotometry no characteristic absorption band assigned to halogen bonding between1\u2009vand NIS was observed."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202102635","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202102635","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202102635","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T10:59:05Z","timestamp":1760266745000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202102635"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,8,26]]},"references-count":95,"journal-issue":{"issue":"56","published-print":{"date-parts":[[2021,10,7]]}},"alternative-id":["10.1002\/chem.202102635"],"URL":"https:\/\/doi.org\/10.1002\/chem.202102635","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,8,26]]},"assertion":[{"value":"2021-07-20","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-08-26","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}