Traceless Benzylic C-H Amination via Bifunctional N-Aminopyridinium Intermediates. Academic Article uri icon


  • C-H amination reactions provide the opportunity to streamline the synthesis of nitrogen-containing organic small molecules. The impact of intermolecular C-H amination methods, however, is currently limited the frequent requirement for the amine precursors to bear activating groups, such as N-sulfonyl substituents, that are both challenging to remove and not useful synthetic handles for subsequent derivatization. Here, we introduce traceless nitrogen activation for C-H amination-which enables application of selective C-H amination chemistry to the preparation of diverse N-functionalized products-via sequential benzylic C-H N-aminopyridylation followed by Ni-catalyzed C-N cross-coupling with aryl boronic acids. Unlike many C-H amination reactions that provide access to protected amines, the current method installs an easily diversifiable synthetic handle that serves as a lynchpin for C-H amination, deaminative N-N functionalization sequences.

published proceedings

  • Angew Chem Int Ed Engl

altmetric score

  • 18.15

author list (cited authors)

  • Roychowdhury, P., Herrera, R. G., Tan, H., & Powers, D. C.

citation count

  • 9

complete list of authors

  • Roychowdhury, Pritam||Herrera, Roberto G||Tan, Hao||Powers, David C

publication date

  • July 2022