Photocatalytic Umpolung Strategy for the Synthesis of α-Amino Phosphine Oxides and Deuterated Derivatives
Chunhua Ma, Xiaofeng Li, Xiya Chen, Xing He, Shuting Zhang, Yuqin Jiang, Bing Yu
Abstract
Direct, economical, and green synthesis of deuterated α-amino phosphine oxides remains an elusive challenge in synthetic chemistry. Herein, we report a visible-light-driven umpolung strategy for synthesizing deuterated α-amino phosphine oxides from isocyanide using 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene as the photocatalyst and D 2 O as the deuterium source. Moreover, the streamlined and sustainable methodology can be applied in the modification of amino acids, natural products, and drugs. The strong antiproliferative activity of the desired products indicates that the method could provide a novel privileged scaffold for antitumor drug development.
Topics & Concepts
UmpolungChemistryPhosphineAmino acidPhotocatalysisDeuteriumCombinatorial chemistryIsocyanideOrganic chemistryCatalysisBiochemistryNucleophileQuantum mechanicsPhysicsAsymmetric Hydrogenation and CatalysisChemical Reactions and IsotopesChemical Synthesis and Analysis