Copper-Catalyzed Electrophilic Etherification of Arylboronic Esters with Isoxazolidines

Seiya Katahara, Tenga Takahashi, Kengo Nomura, Masanobu Uchiyama, Takaaki Sato, Noritaka Chida

Research output: Contribution to journalArticle

Abstract

A copper-catalyzed electrophilic etherification of arylboronic esters is reported. Isoxazolidines are utilized as easily available and stable [RO]+ surrogates to give 1,3-amino aryl ethers. The O-selective arylation of isoxazolidines takes place without causing competitive N-arylation. In contrast to previously reported anionic conditions, our copper-catalyzed conditions are mild enough to achieve high functional group tolerance. Preliminary mechanistic studies and DFT calculations support that the reaction proceeds via a transmetalation/oxidative addition pathway, followed by a Lewis acid-promoted reductive elimination to induce the crucial O-selectivity.

Original languageEnglish
Pages (from-to)1869-1872
Number of pages4
JournalChemistry - An Asian Journal
Volume15
Issue number12
DOIs
Publication statusPublished - 2020 Jun 17

Keywords

  • aryl ether
  • chemoselectivity
  • copper catalyst
  • electrophilic reaction
  • isoxazolidine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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