Photoinduced cobaloxime catalysis enabled dehydrogenative C2-phosphinylation of bicyclo[1.1.0]butanes to access phosphorylated cyclobutenes
Yunong Chang, Fangyu Bian, Jiefei Guo, Miao-Miao Li, Wei Ding
TL;DR
Scientists developed a new light-driven method to modify a type of chemical compound using a catalyst, enabling efficient and selective synthesis of phosphorylated cyclobutenes.
Contribution
A novel photoinduced cobaloxime catalysis method for dehydrogenative C2-phosphinylation of bicyclo[1.1.0]butanes is introduced.
Findings
The reaction operates under mild conditions with high site-selectivity and good yields.
Hydrogen evolution is observed as a byproduct of the phosphinylation process.
Mechanistic studies suggest isomerization and dehydrogenative allylic phosphinylation as key steps.
Abstract
A photoinduced ring-opening radical C2-phosphinylation of bicyclo[1.1.0]butanes with secondary phosphine oxides by cobaloxime catalysis is described. This reaction features mild conditions, wide substrate scope, and high site-selectivities, producing a diverse range of phosphorylated cyclobutenes in good yields with hydrogen evolution. The mechanism studies indicate that this reaction likely proceeds through a bicyclo[1.1.0]butane isomerization and dehydrogenative allylic phosphinylation process. A ring-opening radical C2-phosphinylation of bicyclo[1.1.0]butanes with secondary phosphine oxides is developed by visible-light-induced cobaloxime catalysis.
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Taxonomy
TopicsMetalloenzymes and iron-sulfur proteins · RNA modifications and cancer · Asymmetric Hydrogenation and Catalysis