Hydrosilanes are not always reducing agents for carbonyl compounds, II: Ruthenium-catalyzed deprotection of tert-butyl groups in carbamates, carbonates, esters, and ethers

Shiori Hanada, Akihiro Yuasa, Hirotaka Kuroiwa, Yukihiro Motoyama, Hideo Nagashima

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Hydrosilanes act as a reagent to cleave the C-O bond of OtBu groups in carbamates, carbonates, esters, and ethers by catalysis of a triruthenium cluster. The reaction offers a novel deprotection method, for OiBu groups under neutral conditions, showing unique selectivities that have never been accomplished with conventional Bronsted or Lewis acidic promoters. Possible mechanisms for C-O cleavage are discussed on the basis of NMR spectroscopic analysis.

Original languageEnglish
Pages (from-to)1021-1025
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number6
DOIs
Publication statusPublished - Feb 1 2010

Fingerprint

Carbonyl compounds
carbonyl compounds
Spectroscopic analysis
Ethers
Ruthenium
Carbamates
Carbonates
Reducing Agents
Catalysis
ruthenium
esters
ethers
carbonates
Esters
Nuclear magnetic resonance
spectroscopic analysis
catalysis
reagents
cleavage
selectivity

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Hydrosilanes are not always reducing agents for carbonyl compounds, II : Ruthenium-catalyzed deprotection of tert-butyl groups in carbamates, carbonates, esters, and ethers. / Hanada, Shiori; Yuasa, Akihiro; Kuroiwa, Hirotaka; Motoyama, Yukihiro; Nagashima, Hideo.

In: European Journal of Organic Chemistry, No. 6, 01.02.2010, p. 1021-1025.

Research output: Contribution to journalArticle

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