Hydrosilanes are not always a reducing reagent

A ruthenium-catalyzed introduction of primary alkyl groups to electron-rich aromatic rings using esters as a source of the alkyl groups

Hideo Nagashima, Yuichi Kubo, Mitsunobu Kawamura, Takashi Nishikata, Yukihiro Motoyama

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A triruthenium cluster, (μ 3, η 2, η 3, η 5-acenaphthylene)Ru 3(CO) 7 effectively catalyzes primary-alkylation reaction of electron-rich aromatic rings using a combination of hydrosilane and ester as a source of the primary-alkyl group. The reaction involves electrophilic substitution of arenes by carbocationic species stabilized by a neighboring alkoxy or siloxy group generated during the reduction of esters giving alkylated arenes after reductive removal of the alkoxy or siloxy group at the benzylic position.

Original languageEnglish
Pages (from-to)7667-7672
Number of pages6
JournalTetrahedron
Volume67
Issue number40
DOIs
Publication statusPublished - Oct 7 2011

Fingerprint

Ruthenium
Esters
Electrons
Alkylation
Carbon Monoxide
Substitution reactions
alkoxyl radical
acenaphthylene

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Hydrosilanes are not always a reducing reagent : A ruthenium-catalyzed introduction of primary alkyl groups to electron-rich aromatic rings using esters as a source of the alkyl groups. / Nagashima, Hideo; Kubo, Yuichi; Kawamura, Mitsunobu; Nishikata, Takashi; Motoyama, Yukihiro.

In: Tetrahedron, Vol. 67, No. 40, 07.10.2011, p. 7667-7672.

Research output: Contribution to journalArticle

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