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Fast reactions of N\u2010sulfonyl imidazoliums with carboxylic acids or phosphodiesters formed carboxylic acid\u2010sulfonic acid mixed anhydrides and phospho\u2010sulfonic acid mixed anhydrides, respectively, and the subsequent treatments of the highly active intermediates with the corresponding nucleophilic partners in the presence of imidazoles at room temperature provided amides, dipeptides, carboxylic esters, carboxylic thioesters (almost without racemization during the formation of amides, dipeptides, esters, thioesters), phosphamides, and phosphoesters in high to excellent yields. This kind of N\u2010sulfonyl imidazolium as the coupling reagent was successfully applied in solid phase synthesis of a polypeptide containing 32 amino acid residues. This strategy was effectively extended to the construction of glycosides, and high steroselectivity and good yields were provided. In addition, reactions of N\u2010sulfonyl imidazoliums with amines or alcohols afforded the corresponding sulfonamides and sulfonates in excellent yields. This study should provide a highly efficient, economical, and practical strategy for construction of diverse molecules.<\/jats:p>","DOI":"10.1002\/chem.202501206","type":"journal-article","created":{"date-parts":[[2025,5,6]],"date-time":"2025-05-06T07:55:13Z","timestamp":1746518113000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["<i>N<\/i>\u2010Sulfonyl Imidazoliums as the Versatile Coupling Reagents and Sulfonating Reagents in Synthesis of Amides, Esters, Thioesters, Phosphoramides, Phosphoesters, Glycosides, Sulfonamides, and Sulfonates"],"prefix":"10.1002","volume":"31","author":[{"given":"Hongyun","family":"Li","sequence":"first","affiliation":[{"name":"Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education) Department of Chemistry Tsinghua University  Beijing 100084 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lunyu","family":"Ou","sequence":"additional","affiliation":[{"name":"Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education) Department of Chemistry Tsinghua University  Beijing 100084 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yue","family":"Zhang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education) Department of Chemistry Tsinghua University  Beijing 100084 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weixin","family":"Xiao","sequence":"additional","affiliation":[{"name":"Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education) Department of Chemistry Tsinghua University  Beijing 100084 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhengyi","family":"Yi","sequence":"additional","affiliation":[{"name":"Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education) Department of Chemistry Tsinghua University  Beijing 100084 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yufen","family":"Zhao","sequence":"additional","affiliation":[{"name":"Institute of Drug Discovery Technology Ningbo University  Ningbo 315211 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7250-0053","authenticated-orcid":false,"given":"Hua","family":"Fu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education) Department of Chemistry Tsinghua University  Beijing 100084 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,5,24]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-018-0021-z"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr300220h"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr500193b"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00093-4"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB00638K"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0397658"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201803566"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-020-16477-1"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2SC03989C"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/B701677H"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.2c00005"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/op500305s"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.5b01409"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c00754"},{"key":"e_1_2_7_14_1","volume-title":"The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry and Materials Science","author":"Arthur G.","year":"2000"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/tx200211v"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature10702"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b07230"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.thromres.2017.01.012"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1038\/nprot.2007.454"},{"key":"e_1_2_7_20_1","volume-title":"Comprehensive Organic Transformations: A Guide to Functional Group Preparation","author":"Larock R. 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