Continuous-flow Si-H functionalizations of hydrosilanesviasequential organolithium reactions catalyzed by potassiumtert-butoxide

Hyune Jea Lee, Changmo Kwak, Dong Pyo Kim, Heejin Kim

Research output: Contribution to journalArticlepeer-review

Abstract

We herein report an atom-economic flow approach to the selective and sequential mono-, di-, and tri-functionalizations of unactivated hydrosilanesviaserial organolithium reactions catalyzed by earth-abundant metal compounds. Based on the screening of various additives, we found that catalytic potassiumtert-butoxide (t-BuOK) facilitates the rapid reaction of organolithiums with hydrosilanes. Using a flow microreactor system, various organolithiums bearing functional groups were efficiently generatedin situunder mild conditions and consecutively reacted with hydrosilanes in the presence oft-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.

Original languageEnglish
Pages (from-to)1193-1199
Number of pages7
JournalGreen Chemistry
Volume23
Issue number3
DOIs
Publication statusPublished - 2021 Feb 7

ASJC Scopus subject areas

  • Environmental Chemistry
  • Pollution

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