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Triethylborane-Initiated Room Temperature Radical Addition of Hypophosphites to Olefins:  Synthesis of Monosubstituted Phosphinic Acids and Esters

Sylvine Deprčle and Jean-Luc Montchamp

*Department of Chemistry, Box 298860, Texas Christian University, Fort Worth, Texas 76129, Email: j.montchamptcu.edu

S. Deprčle, J.-L. Montchamp, J. Org. Chem., 2001, 66, 6745-6755.

DOI: 10.1021/jo015876i


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Abstract

A P-centered radical formation initiated by Et3B/O2 provides phosphinic acid derivatives from hypophosphite salts or esters and alkenes at r.t. under neutral conditions. The reaction tolerates a wide range of functional groups. Monosubstituted phosphinic acids obtained in very good isolated yields by a simple extractive workup, but the isolated yields are diminished if a substituent is polar.

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AIBN-Initiated Radical Reactions of Ethyl Phosphinate

M. I. Antczak, J.-L. Montchamp, Synthesis, 2006, 3080-3084.

Palladium-Catalyzed Hydrophosphinylation of Alkenes and Alkynes

S. Deprele, J.-L. Montchamp, J. Am. Chem. Soc., 2002, 124, 9386-9387.


Key Words

phosphinates


ID: J42-Y2001