Utilization of a Trimethylsilyl Group as a Synthetic Equivalent of a Hydroxyl Group via Chemoselective C(sp3)-H Borylation at the Methyl Group on Silicon

Takeru Torigoe, Toshimichi Ohmura, Michinori Suginome

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

A conversion of trimethylsilylalkanes into the corresponding alcohols is established based on an iridium-catalyzed, chemoselective C(sp3)-H borylation of the methyl group on silicon. The (borylmethyl)silyl group formed by C(sp3)-H borylation is treated with H2O2/NaOH, and the resulting (hydroxymethyl)silyl group is converted into a hydroxyl group by Brook rearrangement, followed by oxidation of the resulting methoxysilyl group under Tamao conditions. An alternative route proceeding through the formylsilyl group formed from a (hydroxymethyl)silyl group by Swern oxidation is also established. The method is applicable to substituted trimethylsilylcycloalkanes and 1,1-dimethyl-1-silacyclopentane for conversion into the corresponding stereodefined cycloalkyl alcohols and 1,4-butanediol.

Original languageEnglish
Pages (from-to)2943-2956
Number of pages14
JournalJournal of Organic Chemistry
Volume82
Issue number6
DOIs
Publication statusPublished - Mar 17 2017
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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