Intramolecular S N′-type aromatic substitution of benzylic carbonates at their para-position

Satoshi Ueno, Sadakazu Komiya, Takeshi Tanaka, Ryoichi Kuwano

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

The benzylic carbonates, which connect with an active methine through an o-phenylene tether at their meta-position, are cyclized by Pd(η 3- C 3H 5)Cp-S-Phos catalyst, yielding 3-methyl-9,10- dihydrophenanthrenes. In the catalytic cyclization, the internal nucleophile attacks not the ortho-carbon but the para-carbon of the benzylic ester. The [3 + 2] cycloaddition of m-(silylmethyl)benzyl carbonates with alkylidene malonates was developed from the palladium-catalyzed intramolecular S N′- type aromatic substitution.

Original languageEnglish
Pages (from-to)338-341
Number of pages4
JournalOrganic letters
Volume14
Issue number1
DOIs
Publication statusPublished - Jan 6 2012

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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