Synthesis of o-(diphenylphosphinoyloxy)anilines by the rhodium-catalyzed reaction of nitroarenes and diphenylphosphine oxide

Mieko Arisawa, Manabu Kuwajima, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

A rhodium complex Rh2(OAc)4 catalyzed the reaction of nitrobenzenes and diphenylphosphine oxide HP({double bond, long}O)Ph2 giving o-(diphenylphosphinoyloxy)anilines predominantly, which were accompanied by small amounts of the p-isomers. Nitorobenzenes possessing a bulky o-substituent, particularly o-(t-butyl)nitrobenzenes, underwent the reaction in high yields. The reaction is considered to involve the reductive formation of O-phosphinoyl-N-arylhydroxyamines from nitrobenzenes, and o-phosphinoyloxylation by the rearrangement.

Original languageEnglish
Pages (from-to)3116-3118
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number23
DOIs
Publication statusPublished - 2010 Jun 9

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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