{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T20:03:04Z","timestamp":1791230584293,"version":"4.1.0"},"reference-count":60,"publisher":"Wiley","issue":"35","license":[{"start":{"date-parts":[[2021,6,1]],"date-time":"2021-06-01T00:00:00Z","timestamp":1622505600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100000266","name":"Engineering and Physical Sciences Research Council","doi-asserted-by":"publisher","award":["EP\/ L015838\/1"],"award-info":[{"award-number":["EP\/ L015838\/1"]}],"id":[{"id":"10.13039\/501100000266","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":[[2021,6,21]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Sulfinylamines (R\u2212N=S=O), monoaza analogues of sulfur dioxide, have been known for well over a century, and their reactivity as sulfur electrophiles and in Diels\u2010Alder reactions is well\u2010established. However, they have only rarely been used in organic synthesis in recent decades despite the increasing prominence of compounds containing N=S=O functionality, such as sulfoximines and sulfonimidamides. This Minireview aims to bring wider visibility to the unique chemistry enabled by this class of compounds. We focus on advances from the last 10 years, including the first examples of their use in the one\u2010pot syntheses of sulfoximines and sulfonimidamides. Also covered are the reactions of sulfinylamines with carbon\u2010centred radicals, their use for formation of heterocycles through cycloadditions, and catalytic enantioselective allylic oxidation of alkenes <jats:italic>via<\/jats:italic> a hetero\u2010ene reaction. These examples highlight the different reactivity modes of sulfinylamines and their underappreciated potential for forming molecules which contain high\u2010 or low\u2010valent sulfur, or even no sulfur at all.<\/jats:p>","DOI":"10.1002\/chem.202100321","type":"journal-article","created":{"date-parts":[[2021,4,16]],"date-time":"2021-04-16T11:25:27Z","timestamp":1618572327000},"page":"8918-8927","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":73,"title":["Rediscovering Sulfinylamines as Reagents for Organic Synthesis"],"prefix":"10.1002","volume":"27","author":[{"given":"Thomas Q.","family":"Davies","sequence":"first","affiliation":[{"name":"Chemistry Research Laboratory University of Oxford  12 Mansfield Road Oxford OX1 3TA UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0636-6471","authenticated-orcid":false,"given":"Michael C.","family":"Willis","sequence":"additional","affiliation":[{"name":"Chemistry Research Laboratory University of Oxford  12 Mansfield Road Oxford OX1 3TA UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,6]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.18780110235"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.189002302321"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196200891"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19620740403"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.19717460105"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)89260-6"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19701030225"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1981-29451"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.19582930508"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201708590"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201708590"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2860(99)00453-6"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1293-2558(02)00049-3"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c06986"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar00152a005"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01420a025"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol201957n"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6SC05483H"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b04532"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6SC03924C"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2000-6217"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00208G"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201800273"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201302209"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201610456"},{"key":"e_1_2_8_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201610456"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2016.09.091"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c00960"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.15227\/orgsyn.049.0009"},{"key":"e_1_2_8_27_1","unstructured":"C. McBride L.\u2005L. Trzoss A. Boloor N. Sokolova R.\u2005M. Pastor S.\u2005T. Staben C. Stivala M. Volgraf S.\u2005M. Bronner (Genentech Inc.) WO2020\/018975 2020."},{"key":"e_1_2_8_28_1","unstructured":"M.\u2005J. Tilby A. Hall C. Mart\u00ednez-Lamenca M.\u2005C. Willis unpublished work."},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b06831"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00832a026"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201201945"},{"key":"e_1_2_8_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201201945"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c03505"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201911075"},{"key":"e_1_2_8_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201911075"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201700501"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo0490245"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102488"},{"key":"e_1_2_8_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201102488"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja045694g"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature22805"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01078a047"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr900382t"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201911021"},{"key":"e_1_2_8_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201911021"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CS00483A"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00761"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b00143"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201904543"},{"key":"e_1_2_8_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201904543"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201810887"},{"key":"e_1_2_8_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201810887"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CC08274K"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201804346"},{"key":"e_1_2_8_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201804346"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2007.11.131"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1039\/C0DT01133A"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202100321","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202100321","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202100321","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T15:39:32Z","timestamp":1760283572000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202100321"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,6]]},"references-count":60,"journal-issue":{"issue":"35","published-print":{"date-parts":[[2021,6,21]]}},"alternative-id":["10.1002\/chem.202100321"],"URL":"https:\/\/doi.org\/10.1002\/chem.202100321","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,6]]},"assertion":[{"value":"2021-01-26","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-06-01","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}