Traceless Benzylic CH Amination via Bifunctional NAminopyridinium Intermediates Academic Article uri icon

abstract

  • AbstractCH amination reactions provide the opportunity to streamline the synthesis of nitrogencontaining organic small molecules. The impact of intermolecular CH amination methods, however, is currently limited the frequent requirement for the amine precursors to bear activating groups, such asNsulfonyl substituents, that are both challenging to remove and not useful synthetic handles for subsequent derivatization. Here, we introduce traceless nitrogen activation for CH aminationwhich enables application of selective CH amination chemistry to the preparation of diverseNfunctionalized productsvia sequential benzylic CHNaminopyridylation followed by Nicatalyzed CN crosscoupling with aryl boronic acids. Unlike many CH amination reactions that provide access to protected amines, the current method installs an easily diversifiable synthetic handle that serves as a lynchpin for CH amination, deaminative NN functionalization sequences.

published proceedings

  • Angewandte Chemie

author list (cited authors)

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

citation count

  • 1

complete list of authors

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

publication date

  • July 2022

publisher