(Diazomethyl)dimethylphosphine Oxide - A Diazoalkane Reagent for [3+2] Cycloadditions.

Authors :: Slobodyanyuk EY
Tarasiuk I
Pasichnyk T
Volochnyuk DM
Sibgatulin DO
Grygorenko OO
Source :: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Apr 22; Vol. 30 (23), pp. e202303972. Date of Electronic Publication: 2024 Mar 08.
Publication Year :: 2024
Abstract: A safe and efficient method for the in-situ preparation of (diazomethyl)dimethylphosphine oxide - a hereto unexplored diazoalkane reagent - is developed. The method is based on the diazotization of the corresponding P(O)Me <subscript>2</subscript> -substituted amine (readily available in multigram quantities) in non-aqueous media. The protocol provides the target product as ca. 1.5 M CHCl <subscript>3</subscript> solution which is stable at -18 °C. The utility of the synthesized diazoalkane is illustrated by its [3+2] cycloaddition with electron-poor alkynes and alkenes providing the corresponding P(O)Me <subscript>2</subscript> -substituted pyrazoles and pyrazolines with moderate to good efficiency. In this view, the title compound represents and an important extension of medicinally relevant phosphine oxide reagents.<br /> (© 2024 Wiley‐VCH GmbH.)

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