A superior method for the reduction of secondary phosphine oxides |
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Authors: | Busacca Carl A Lorenz Jon C Grinberg Nelu Haddad Nizar Hrapchak Matt Latli Bachir Lee Heewon Sabila Paul Saha Anjan Sarvestani Max Shen Sherry Varsolona Richard Wei Xudong Senanayake Chris H |
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Affiliation: | Department of Chemical Development, Boehringer-Ingelheim Pharmaceuticals Inc., 900 Ridgebury Road, Ridgefield, Connecticut 06877, USA. cbusacca@rdg.boehringer-ingelheim.com |
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Abstract: | [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. |
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