- Intensified Continuous Flow Michaelis-Arbuzov Rearrangement toward Alkyl Phosphonates
-
Herein is described the development of an intensified continuous flow process for the preparation of a library of alkyl phosphonates through a Michaelis-Arbuzov rearrangement. A careful process optimization and thorough analysis of the competitive reactions led to a very attractive protocol with unprecedented productivities (up to 4.97 kg of material per day) and a low environmental footprint with the absence of solvent, additives, catalysts, and waste. In-line low-field 31P NMR monitoring was conveniently implemented for rapid optimization and process monitoring. Two key alkyl phosphonate intermediates were also assessed for the unprecedented diazene dicarboxylate-mediated electrophilic amination under continuous flow conditions toward the α-aminophosphonic acid derivatives of Pphenylalanine and Palanine, bioisosters of the natural amino acids phenylalanine and alanine, respectively.
- Monbaliu, Jean-Christophe M.,Toupy, Thomas
-
supporting information
p. 467 - 478
(2022/02/25)
-
- Reactions of α-boranophosphorus compounds with electrophiles: Alkylation, acylation, and other reactions
-
(Chemical Equation Presented) The homologation of phosphorus carbenoids with organoboranes leads to α-boranophosphorus compounds, which can be further functionalized through reactions with various electrophiles, either directly or after activation to the
- Antczak, Monika I.,Montchamp, Jean-Luc
-
supporting information; experimental part
p. 3758 - 3766
(2009/11/30)
-