Chemoselective synthesis of long-chain alkyl- H-phosphinic acids via one-pot alkylation/oxidation of red phosphorus with alkyl-PEGs as recyclable micellar catalysts

Vladimir A Kuimov; Svetlana F Malysheva; Natalia A Belogorlova; Nina K Gusarova; Boris A Trofimov

doi:10.1039/d1ob01470f

Chemoselective synthesis of long-chain alkyl- H-phosphinic acids via one-pot alkylation/oxidation of red phosphorus with alkyl-PEGs as recyclable micellar catalysts

Org Biomol Chem. 2021 Dec 15;19(48):10587-10595. doi: 10.1039/d1ob01470f.

Authors

Vladimir A Kuimov¹, Svetlana F Malysheva¹, Natalia A Belogorlova¹, Nina K Gusarova¹, Boris A Trofimov¹

Affiliation

¹ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia. [email protected].

PMID: 34542128
DOI: 10.1039/d1ob01470f

Abstract

Long-chain n-alkyl-H-phosphinic acids (Alk = C₄-C₁₈) are chemoselectively synthesized in yields up to 90% via the direct one-pot alkylation/oxidation of red phosphorus (P_n) in the multi-phase alkyl bromide/KOH/H₂O/toluene system with alkyl-PEG recyclable micellar catalysts, which demonstrate good recyclability.