Metal-Free Conversion of Methane and Cycloalkanes to Amines and Amides by Employing a Borylnitrene


  • This work was supported by the DFG and the Fonds der Chemischen Industrie. We thank Professor Wolfram Sander for his interest and support of this work, and Patrik Neuhaus for the ESR measurements.


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C[BOND]H insertion: Borylnitrenes, which are generated in situ by photoylsis of azides, convert unactivated alkanes by intermolecular C[BOND]H insertion into aminoboranes (see scheme), which in turn can be reacted further to give amines or amides. The boryl group serves two purposes: it converts the nitrene into a highly reactive BN vinylidene analogue, and it is easily cleaved from the product.