Continuous-flow Si–H functionalizations of hydrosilanes via sequential organolithium reactions catalyzed by potassium tert-butoxide. Issue 3 (25th November 2020)

• Record Type: Journal Article
• Authors: Lee, Hyune-Jea; Kwak, Changmo; Kim, Dong-Pyo; Kim, Heejin
• Is Part Of: Green chemistry. Volume 23:Issue 3(2021)
• Page Start: 1193
• Page End: 1199
• Publication Date: 2020-11-25
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/d0gc03213a
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : We herein report an atom-economic flow approach to the selective and sequential mono-, di-, and tri-functionalizations of unactivated hydrosilanes via serial organolithium reactions catalyzed by earth-abundant metal compounds. Abstract : We herein report an atom-economic flow approach to the selective and sequential mono-, di-, and tri-functionalizations of unactivated hydrosilanes via serial organolithium reactions catalyzed by earth-abundant metal compounds. Based on the screening of various additives, we found that catalytic potassium tert -butoxide ( t -BuOK) facilitates the rapid reaction of organolithiums with hydrosilanes. Using a flow microreactor system, various organolithiums bearing functional groups were efficiently generated in situ under mild conditions and consecutively reacted with hydrosilanes in the presence of t -BuOK within 1 min. We also successfully conducted the di-funtionalizations of dihydrosilane by sequential organolithium reactions, extending to a gram-scale-synthesis. Finally, the combinatorial functionalizations of trihydrosilane were achieved to give every conceivable combination of tetrasubstituted organosilane libraries based on a precise reaction control using an integrated one-flow system.