Speaker
Description
Microreactor technology and flow chemistry could play an important role in the development of green and sustainable synthetic processes.1 In this presentation, some recent relevant examples in the field of flash chemistry, catalysis, hazardous chemistry and continuous flow processing of metallated species are described.2 Selected examples highlight the role that flow chemistry could play in the near future for a sustainable development. In addition, this overview focusses on new synthetic tactics for the straightforward preparation of hardly accessible structural motifs and functional groups of sulfur (IV) and (VI) as sulfilimines, sulfinimidates, sulfinamidines and sulfinamide esters, by using simple metal-free protocols in bench and flow conditions. 3 In situ FT-IR investigations and quantum mechanical/nuclear magnetic resonance (NMR) approaches are widely used for the mechanistic hypothesis of studied reactions as well as for structural and configurational assignment of isolated organic compounds generally supported also by crystallographic analysis.
1) Fanelli, F., Parisi, G., Degennaro, L., Luisi, R. Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis (2017) Beilstein Journal of Organic Chemistry, 13, pp. 520-542.
2) a) Musci, P., von Keutz, T., Belaj, F., Degennaro, L., Cantillo, D., Kappe, C.O., Luisi, R. Flow Technology for Telescoped Generation, Lithiation and Electrophilic (C3) Functionalization of Highly Strained 1-Azabicyclo[1.1.0]butanes (2021) Angewandte Chemie - International Edition, 60 (12), pp. 6395-6399. b) Colella, M., Musci, P., Cannillo, D., Spennacchio, M., Aramini, A., Degennaro, L., Luisi, R. Development of a Continuous Flow Synthesis of 2-Substituted Azetines and 3-Substituted Azetidines by Using a Common Synthetic Precursor (2021) Journal of Organic Chemistry, 86 (20), pp. 13943-13954. c) Colella, M., Tota, A., Takahashi, Y., Higuma, R., Ishikawa, S., Degennaro, L., Luisi, R., Nagaki, A. Fluoro-Substituted Methyllithium Chemistry: External Quenching Method Using Flow Microreactors (2020) Angewandte Chemie - International Edition, 59 (27), pp. 10924-10928. d) Monticelli, S., Colella, M., Pillari, V., Tota, A., Langer, T., Holzer, W., Degennaro, L., Luisi, R., Pace, V. Modular and Chemoselective Strategy for the Direct Access to α-Fluoroepoxides and Aziridines via the Addition of Fluoroiodomethyllithium to Carbonyl-Like Compounds (2019) Organic Letters, 21 (2), pp. 584-588.
3) a) Zenzola, M., Doran, R., Degennaro, L., Luisi, R., Bull, J.A. Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides (2016) Angewandte Chemie - International Edition, 55 (25), pp. 7203-7207. b) Andresini, M., Tota, A., Degennaro, L., Bull, J.A., Luisi, R. Synthesis and Transformations of NH-Sulfoximines (2021) Chemistry - A European Journal, 27 (69), pp. 17293-17321. c) Andresini, M., Spennacchio, M., Colella, M., Losito, G., Aramini, A., Degennaro, L., Luisi, R. Sulfinimidate Esters as an Electrophilic Sulfinimidoyl Motif Source: Synthesis of N-Protected Sulfilimines from Grignard Reagents (2021) Organic Letters, 23 (17), pp. 6850-6854. d) Andresini, M., Colella, M., Degennaro, L., Luisi, R. Hypervalent iodine (III) reagents and ammonia as useful combination for highly chemoselective N-transfer to low-valent organosulfur compounds and amines (2021) Arkivoc, 2022 (4).
