Synthesis of sulfonimidamides from sulfinamides by oxidation with N-chlorosuccinimide

Scholarly Works

• Athawale, P. R.; Shultz, Z. P.; Saputo, A.; Hall, Y. D.; Lopchuk, J. M. Strain-release driven reactivity of a chiral SuFEx reagent provides stereocontrolled access to sulfinamides, sulfonimidamides, and sulfoximines. Nature communications 2024, 15, 7001. doi:10.1038/s41467-024-51224-w
• Proietti, G.; Axelsson, A.; Capezza, A. J.; Todarwal, Y.; Kuzmin, J.; Linares, M.; Norman, P.; Szabó, Z.; Lendel, C.; Olsson, R. T.; Dinér, P. Ultralight aerogels via supramolecular polymerization of a new chiral perfluoropyridine-based sulfonimidamide organogelator. Nanoscale 2024, 16, 7603–7611. doi:10.1039/d3nr06460c
• Yan, M.; Wang, S.-F.; Zhang, Y.-P.; Zhao, J.-Z.; Tang, Z.; Li, G.-X. Synthesis of sulfinamides via photocatalytic alkylation or arylation of sulfinylamine. Organic & biomolecular chemistry 2024, 22, 348–352. doi:10.1039/d3ob01782f
• Pan, S.; Mulks, F. F.; Wu, P.; Rissanen, K.; Bolm, C. Mechanochemical Iron‐Catalyzed Nitrene Transfer Reactions: Direct Synthesis of N‐Acyl Sulfonimidamides from Sulfinamides and Dioxazolones. Angewandte Chemie 2023, 136. doi:10.1002/ange.202316702
• Pan, S.; Mulks, F. F.; Wu, P.; Rissanen, K.; Bolm, C. Mechanochemical Iron-Catalyzed Nitrene Transfer Reactions: Direct Synthesis of N-Acyl Sulfonimidamides from Sulfinamides and Dioxazolones. Angewandte Chemie (International ed. in English) 2023, 63, e202316702. doi:10.1002/anie.202316702
• Li, L.; Zhang, S.-q.; Chen, Y.; Cui, X.; Zhao, G.; Tang, Z.; Li, G.-x. Photoredox Alkylation of Sulfinylamine Enables the Synthesis of Highly Functionalized Sulfinamides and S(VI) Derivatives. ACS Catalysis 2022, 12, 15334–15340. doi:10.1021/acscatal.2c05169
• Ding, M.; Zhang, Z.-X.; Davies, T. Q.; Willis, M. C. A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides. Organic letters 2022, 24, 1711–1715. doi:10.1021/acs.orglett.2c00347
• Passia, M. T.; Schöbel, J.-H.; Lentelink, N. J.; Truong, K.-N.; Rissanen, K.; Bolm, C. Synthesis of trifluoromethyl-substituted 1,2,6-thiadiazine 1-oxides from sulfonimidamides under mechanochemical conditions. Organic & biomolecular chemistry 2021, 19, 9470–9475. doi:10.1039/d1ob01912k
• Lo, P. K. T.; Willis, M. C. Nickel(II)-Catalyzed Addition of Aryl and Heteroaryl Boroxines to the Sulfinylamine Reagent TrNSO: The Catalytic Synthesis of Sulfinamides, Sulfonimidamides, and Primary Sulfonamides. Journal of the American Chemical Society 2021, 143, 15576–15581. doi:10.1021/jacs.1c08052
• Liu, Y.; Pan, Q.; Hu, X.; Guo, Y.; Chen, Q.-Y.; Liu, C. Rapid Access to N-Protected Sulfonimidoyl Fluorides: Divergent Synthesis of Sulfonamides and Sulfonimidamides. Organic letters 2021, 23, 3975–3980. doi:10.1021/acs.orglett.1c01118
• Chatterjee, S.; Makai, S.; Morandi, B. Hydroxylamine-Derived Reagent as a Dual Oxidant and Amino Group Donor for the Iron-Catalyzed Preparation of Unprotected Sulfinamides from Thiols. Angewandte Chemie (International ed. in English) 2020, 60, 758–765. doi:10.1002/anie.202011138
• Chatterjee, S.; Makai, S.; Morandi, B. Hydroxylamin‐abgeleitetes Reagenz als duales Oxidationsmittel und Aminogruppendonor für die eisenkatalysierte Herstellung von ungeschützten Sulfinamiden aus Thiolen. Angewandte Chemie 2020, 133, 769–776. doi:10.1002/ange.202011138
• Wojaczyńska, E.; Wojaczyński, J. Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds. Chemical reviews 2020, 120, 4578–4611. doi:10.1021/acs.chemrev.0c00002
• Agarwal, S.; Sasane, S.; Shah, H. A.; Pethani, J. P.; Deshmukh, P. K.; Vyas, V.; Iyer, P.; Bhavsar, H.; Viswanathan, K.; Bandyopadhyay, D.; Giri, P.; Mahapatra, J.; Chatterjee, A.; Jain, M. R.; Sharma, R. P. Discovery of N-Cyano-sulfoximineurea Derivatives as Potent and Orally Bioavailable NLRP3 Inflammasome Inhibitors. ACS medicinal chemistry letters 2020, 11, 414–418. doi:10.1021/acsmedchemlett.9b00433.s001
• Bremerich, M.; Conrads, C. M.; Langletz, T.; Bolm, C. Additions to N‐Sulfinylamines as an Approach for the Metal‐free Synthesis of Sulfonimidamides: O‐Benzotriazolyl Sulfonimidates as Activated Intermediates. Angewandte Chemie 2019, 131, 19190–19196. doi:10.1002/ange.201911075
• Bremerich, M.; Conrads, C.; Langletz, T.; Bolm, C. Additions to N‐Sulfinylamines as an Approach for the Metal‐free Synthesis of Sulfonimidamides: O‐Benzotriazolyl Sulfonimidates as Activated Intermediates. Angewandte Chemie (International ed. in English) 2019, 58, 19014–19020. doi:10.1002/anie.201911075
• Ghahremani, M.; Bahrami, H.; Douroudgari, H.; Vahedpour, M. Theoretical prediction of proton and electron affinities, gas phase basicities, and ionization energies of sulfinamides. Structural Chemistry 2019, 31, 411–421. doi:10.1007/s11224-019-01401-1
• Zhang, Z.-X.; Davies, T. Q.; Willis, M. C. Modular Sulfondiimine Synthesis Using a Stable Sulfinylamine Reagent. Journal of the American Chemical Society 2019, 141, 13022–13027. doi:10.1021/jacs.9b06831
• Chinthakindi, P. K.; Benediktsdottir, A.; Ibrahim, A.; Wared, A.; Aurell, C.-J.; Pettersen, A.; Zamaratski, E.; Arvidsson, P. I.; Chen, Y.; Sandström, A. Synthesis of Sulfonimidamide‐Based Amino Acid Building Blocks with Orthogonal Protecting Groups. European Journal of Organic Chemistry 2019, 2019, 1045–1057. doi:10.1002/ejoc.201801541
• Yu, H.; Li, Z.; Bolm, C. Copper‐Catalyzed Transsulfinamidation of Sulfinamides as a Key Step in the Preparation of Sulfonamides and Sulfonimidamides. Angewandte Chemie 2018, 130, 15828–15831. doi:10.1002/ange.201810548

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