Precipiton reagents: precipiton phosphines for solution-phase reductions

Organic Letters
Todd Bosanac, Craig S Wilcox

Abstract

[structure: see text] [structure: see text] [structure: see text] Several Precipiton phosphines were prepared and employed in the Staudinger reaction and in the reduction of secondary ozonides. Both amines and aldehdyes were obtained in good to excellent yields and purities. After use of the phosphine, isomerization and precipitation of the spent phosphorus reagent were induced by exposure to visible light in the presence of erythrosin B, a triplet sensitizer. Products were isolated by simple filtration. The use of the triplet sensitizer has the added advantage of eliminating [2 + 2] cycloaddition reactions between trans-Precipitons.

References

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Sep 15, 2000·Organic Letters·A G BarrettJ Schröder
Oct 25, 2001·The Journal of Organic Chemistry·Hélène Perrier, Marc Labelle
Apr 19, 2002·Journal of the American Chemical Society·Todd Bosanac, Craig S Wilcox
Sep 21, 2002·Chemical Communications : Chem Comm·T Bosanac, C S Wilcox
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Citations

Dec 1, 2011·Nucleic Acids Research·Chikara DohnoKazuhiko Nakatani
May 2, 2015·Chemical Communications : Chem Comm·Mirko LohseStefan Hecht
Mar 12, 2010·Chemical Communications : Chem Comm·Steven E Dickson, Cathleen M Crudden
Apr 25, 2015·Angewandte Chemie·Kazuyuki MoriMakoto Fujita
Jul 5, 2018·The Journal of Physical Chemistry. a·Guanyu ZhangM Graça H Vicente
Jan 5, 2006·Journal of the American Chemical Society·Mark R Ams, Craig S Wilcox
Nov 15, 2005·Journal of Combinatorial Chemistry·Roland E Dolle

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