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

A rhodium complex Rh2(OAc)4 catalyzed the reaction of nitrobenzenes and diphenylphosphine oxide HP(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)nitrobe...

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Bibliographic Details
Published inTetrahedron letters Vol. 51; no. 23; pp. 3116 - 3118
Main Authors Arisawa, Mieko, Kuwajima, Manabu, Yamaguchi, Masahiko
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 09.06.2010
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REARRANGEMENT
ORGANOSULFUR COMPOUNDS
SOLUTION CHEMISTRY
CARCINOGENS
HYDROLYSIS
PHENYLHYDROXYLAMINES
MODEL
AROMATIC-AMINES
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Summary:A rhodium complex Rh2(OAc)4 catalyzed the reaction of nitrobenzenes and diphenylphosphine oxide HP(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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.04.029