An overview of the synthesis of phosphinates and phosphinic amides

Nóra Z. Kiss, G. Keglevich

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The possibilities for the synthesis of phosphinic esters (phosphinates) and phosphinic amides, useful starting materials and intermediates, are discussed. The classical method involves the use of phosphinic chlorides in reaction with the alcohol/ phenol or amine as the nucleophile. A “greener” approach may start from phosphinic acids, however, their direct esterification and amidation are not possible on conventional heating. According to a novel observation, the direct derivatizations (especially esterifications) still take place under microwave conditions. Another possibility is the alkylating esterification by alkyl halides to afford phosphinates. Phase transfer catalysis may be a useful tool to make such transformations possible. According to another strategy, the phosphinic acids are converted to more active intermediates that may then react with the O- and N-nucleophile efficiently. Among the activating agents, the T3P® reagent is the most noteworthy one. Among the other methods discussed, Arbuzov reaction and the fragmentation-related phosphinylations of O- and N-nucleophiles are underlined. It is interesting that there have not been real reviews in this field, although phosphinic starting materials and intermediates are utilized commonly in synthetic organic chemistry.

Original languageEnglish
Pages (from-to)2673-2690
Number of pages18
JournalCurrent Organic Chemistry
Volume18
Issue number21
Publication statusPublished - Jan 1 2014

Fingerprint

Nucleophiles
Esterification
Phosphinic Acids
Amides
Phenol
Catalysis
Amines
Chlorides
Esters
Microwaves
Alcohols
Heating

Keywords

  • Activating agents
  • Microwave
  • Phase transfer catalysis
  • Phosphinates
  • Phosphinic acids
  • Phosphinic amides

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

An overview of the synthesis of phosphinates and phosphinic amides. / Kiss, Nóra Z.; Keglevich, G.

In: Current Organic Chemistry, Vol. 18, No. 21, 01.01.2014, p. 2673-2690.

Research output: Contribution to journalArticle

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