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Recent Advances of the Atherton-Todd Reaction

Siqiang Fang, Zanjiao Liu, Tianli Wang

2023Chinese Journal of Organic Chemistry12 citationsDOIOpen Access PDF

Abstract

Phosphoramides or phosphates and their derivatives are a very important class of phosphorus-containing organic molecules, which are widely applied in medicinal chemistry, material chemistry and organic catalysis.As one of the most effective methods towards constructing phosphorus compounds, the Atherton-Todd reaction involves in situ halogenation of P(O)-H molecules with tetrachloromethane to generate the key intermediates of phosphoryl chlorides in the presence of bases, which subsequently react with amines or alcohols to form the corresponding phosphoramide or phosphate products.In recent years, this reaction has been widely explored by synthetic chemists due to its ease of operation, high atom economy, broad substrate versatility, and ease of incorporation of phosphorus units into active structural fragments.The research progress of the Atherton-Todd reaction and its application in organic synthesis in recent decades are summarized, and a brief outlook on the current research challenges is put forward, hoping to provide reference and thinking for the further development of the Atherton-Todd reaction.

Topics & Concepts

ChemistryComputational chemistryAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality SynthesisFluorine in Organic Chemistry