Hydrogen isotope exchange reactions involving C–H (D, T) bonds

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Thomas Junk and W. James Catallo


Abstract

Exchange reactions involving the displacement of hydrogen bonded to carbon by its heavier isotopes are of interest for both mechanistic and product-orientated research. This review surveys practical strategies for the preparation of isotopically labelled compounds, discusses recent progress made in developing mild and regioselective exchange protocols, and summarizes the mechanistic aspects of C–H bond activation under homogeneous and heterogeneous exchange conditions.


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