A superior method for the reduction of secondary phosphine oxides.
[reaction: see text] Diisobutylaluminum hydride (DIBAL-H) and triisobutylaluminum have been found to be outstanding reductants for secondary phosphine oxides (SPOs). All classes of SPOs can be readily reduced, including diaryl, arylalkyl, and dialkyl members. Many SPOs can now be reduced at cryogenic temperatures, and conditions for preservation of reducible functional groups have been found. Even the most electron-rich and sterically hindered phosphine oxides can be reduced in a few hours at 50-70 degrees C. This new reduction has distinct advantages over existing technologies.
Busacca
Carl A
CA
Department of Chemical Development, Boehringer-Ingelheim Pharmaceuticals Inc., 900 Ridgebury Road, Ridgefield, Connecticut 06877, USA. cbusacca@rdg.boehringer-ingelheim.com
Lorenz
Jon C
JC
Grinberg
Nelu
N
Haddad
Nizar
N
Hrapchak
Matt
M
Latli
Bachir
B
Lee
Heewon
H
Sabila
Paul
P
Saha
Anjan
A
Sarvestani
Max
M
Shen
Sherry
S
Varsolona
Richard
R
Wei
Xudong
X
Senanayake
Chris H
CH
D000535:Aluminum / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010087:Oxides / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*
D008024:Ligands; D010087:Oxides; D010720:Phosphines; D000535:Aluminum; C044646:phosphine