Literature DB >> 16146406

A superior method for the reduction of secondary phosphine oxides.

Carl A Busacca1, Jon C Lorenz, Nelu Grinberg, Nizar Haddad, Matt Hrapchak, Bachir Latli, Heewon Lee, Paul Sabila, Anjan Saha, Max Sarvestani, Sherry Shen, Richard Varsolona, Xudong Wei, Chris H Senanayake.   

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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Year:  2005        PMID: 16146406     DOI: 10.1021/ol0517832

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides.

Authors:  Nolan T McDougal; Jan Streuff; Herschel Mukherjee; Scott C Virgil; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2010-10-20       Impact factor: 2.415

2.  A general enantioselective route to the chamigrene natural product family.

Authors:  David E White; Ian C Stewart; Brinton A Seashore-Ludlow; Robert H Grubbs; Brian M Stoltz
Journal:  Tetrahedron       Date:  2010-03-26       Impact factor: 2.457

3.  Water-soluble phosphinothiols for traceless staudinger ligation and integration with expressed protein ligation.

Authors:  Annie Tam; Matthew B Soellner; Ronald T Raines
Journal:  J Am Chem Soc       Date:  2007-08-22       Impact factor: 15.419

4.  Scope and Limitations of the s-Block Metal-Mediated Pudovik Reaction.

Authors:  Benjamin E Fener; Philipp Schüler; Nico Ueberschaar; Peter Bellstedt; Helmar Görls; Sven Krieck; Matthias Westerhausen
Journal:  Chemistry       Date:  2020-05-11       Impact factor: 5.236

5.  Ortho-Phosphinoarenesulfonamide-Mediated Staudinger Reduction of Aryl and Alkyl Azides.

Authors:  Xingzhuo Li; Zhenguo Wang; Wenjun Luo; Zixu Wang; Keshu Yin; Le Li
Journal:  Molecules       Date:  2022-09-05       Impact factor: 4.927

6.  Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions.

Authors:  Xia Fan; Rongshun Chen; Jie Han; Zhengjie He
Journal:  Molecules       Date:  2019-12-16       Impact factor: 4.411

7.  Palladium-Catalyzed C-P Bond-Forming Reactions of Aryl Nonaflates Accelerated by Iodide.

Authors:  Holly McErlain; Leanne M Riley; Andrew Sutherland
Journal:  J Org Chem       Date:  2021-11-02       Impact factor: 4.354

  7 in total

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