Multideuteration of Nitroaromatics by Silver-Catalyzed Hydrogen-Isotope Exchange



A silver-catalyzed deuteration of nitroaromatics has been achieved using D2O as the deuterium source. Distinct from the well-established directing group guided hydrogen-isotope exchange, the protocol showed an interesting deuteration pattern, where considerable deuterium accumulation was observed around the aromatic rings. Controlling experiments suggested that the deuteration was initiated by a silver-promoted C-H activation. Therefore a tentative two-stage deuteration mechanism involving aryl-silver species was proposed to explain the deuteration on meta- and para-positions.

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Supplementary material

Supporting Information
Experimental data, deuterium incorporation determination, copies of spectrum, and calculation details could be found in supporting information.