A (Borylmethyl)silane Bearing Three Hydrolyzable Groups on Silicon: Synthesis via Iridium-Catalyzed C(sp3)-H Borylation and Conversion to Functionalized Siloxanes

Toshimichi Ohmura, Ikuo Sasaki, Takeru Torigoe, Michinori Suginome

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

An iridium-catalyzed C(sp3)-H borylation of X3SiMe (X = hydrolyzable group) was established. A trialkoxy(methyl)silane bearing sterically demanding neopentyloxy groups (X = neopentyloxy) underwent C-H borylation at the methyl group on silicon, giving (borylmethyl)tris(neopentyloxy)silane in 70% isolated yield. The choice of the hydrolyzable group X was the key to efficient and chemoselective C-H borylation; trialkoxy(methyl)silanes bearing sterically less demanding alkoxy groups (X = ethoxy, n-butyloxy, and isobutyloxy) suffered from C-H activation at the alkoxy groups, and trichloro(methyl)silane (X = Cl) failed to react. A trimethylsiloxy group could substitute the neopentyloxy groups of the borylated product by the reaction of trimethylsilanol in the presence of tetrabutylammonium fluoride.

Original languageEnglish
Pages (from-to)1601-1603
Number of pages3
JournalOrganometallics
Volume35
Issue number11
DOIs
Publication statusPublished - Jun 13 2016
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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