TY - JOUR
T1 - Synthesis of o-(diphenylphosphinoyloxy)anilines by the rhodium-catalyzed reaction of nitroarenes and diphenylphosphine oxide
AU - Arisawa, Mieko
AU - Kuwajima, Manabu
AU - Yamaguchi, Masahiko
N1 - Funding Information:
This work was supported by Grant-in-Aid for Scientific Research (No. 21229001 ), GCOE program , and WPI Initiative from JSPS. M.A. expresses her thanks to the Grant-in-Aid for Scientific Research on Priority Areas, ‘Advanced Molecular Transformation of Carbon Resources’ from MEXT (Nos. 18037005 and 19020008 ) and Naito Foundation.
PY - 2010/6/9
Y1 - 2010/6/9
N2 - 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.
AB - 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.
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U2 - 10.1016/j.tetlet.2010.04.029
DO - 10.1016/j.tetlet.2010.04.029
M3 - Article
AN - SCOPUS:77953123407
SN - 0040-4039
VL - 51
SP - 3116
EP - 3118
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 23
ER -