The present invention provides a
samarium diiodide-mediated
cyclopropane ring-opening and deuteration method and application, comprising the following steps: preparing a
samarium diiodide solution; sequentially adding a
nitrogen-containing alkaline compound and a
deuterium source to the solution; subsequently adding an ester substrate, stirring the solution for reaction, and bubbling air to oxidize the excess
samarium; sequentially adding
dichloromethane and
hydrochloric acid, diluting, separating the
layers, and extracting the aqueous layer with an extractant; combining the remaining organic
layers,
drying, filtering, and then distilling under reduced pressure to purify the residue. This method utilizes inexpensive
heavy water as a
deuterium donor, combining SmI2-promoted
cyclopropane ring-opening with the reduction of a
carboxylic acid derivative to achieve deuteration reactions at multiple positions. Furthermore, the SmI2 / D2O
system exhibits significantly broader substrate compatibility. By adjusting the
reagent dosage to form different strategies for
cyclopropane ring-opening and reductive deuteration,
deuterium can be efficiently introduced into a variety of substrates, including ketones, esters, nitriles, acyl chlorides, acyl fluorides, and oximes.