Reduction of Tertiary Phosphine Oxides with DIBAL-H.

Reduction of Tertiary Phosphine Oxides with DIBAL-H. Research Abstract Details 

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Reduction of Tertiary Phosphine Oxides with DIBAL-H. Abstract Text:

Carl A Busacca,Ravinder Raju,Nelu Grinberg,Nizar Haddad,Paul James-Jones,Heewon Lee,Jon C Lorenz,Anjan Saha,Chris H Senanayake,Carl A Busacca,Ravinder Raju,Nelu Grinberg,Nizar Haddad,Paul James-Jones,Heewon Lee,Jon C Lorenz,Anjan Saha,Chris H Senanayake,

The reduction of tertiary phosphine oxides (TPOs) and sulfides with diisobutylaluminum hydride (DIBAL-H) has been studied in detail. An extensive solvent screen has revealed that hindered aliphatic ethers, such as MTBE, are optimum for this reaction at ambient temperature. Many TPOs undergo considerable reduction at ambient temperature and then stall due to inhibition. 31P and 13C NMR studies using isotopically labeled substrates as well as competition studies have revealed that the source of this inhibition is tetraisobutyldialuminoxane (TIBAO), which builds up as the reaction proceeds. TIBAO selectively coordinates the TPO starting material, preventing further reduction. Several strategies have been found to circumvent this inhibition and obtain full conversion with this extremely inexpensive reducing agent for the first time. Practical reduction protocols for these critical targets have been developed.

Reduction of Tertiary Phosphine Oxides with DIBAL-H. Publishing Authors By Initials

CA Busacca,R Raju,N Grinberg,N Haddad,P James-Jones,H Lee,JC Lorenz,A Saha,CH Senanayake,CA Busacca,R Raju,N Grinberg,N Haddad,P James-Jones,H Lee,JC Lorenz,A Saha,CH Senanayake,

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Reduction of Tertiary Phosphine Oxides with DIBAL-H. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: The Journal of organic chemistry

VOLUME: 73

Page Numbers: 1524-31

Journal Abbreviation: J. Org. Chem.

ISSN: 0022-3263

DAY: 16

MONTH: 01

YEAR: 2008

Reduction of Tertiary Phosphine Oxides with DIBAL-H. Information

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LANGUAGE: eng

NlmUniqueID: 2985193

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Grant and Affiliation Information for Reduction of Tertiary Phosphine Oxides with DIBAL-H.

AFFILIATION: Department of Chemical Development, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, Connecticut 06877.

Country: United States

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MEDLINETA: J Org Chem

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