Palladium-Catalyzed Ring-Closing Reaction via C-N Bond Metathesis for Rapid Construction of Saturated N-Heterocycles

J Am Chem Soc. 2020 Oct 28;142(43):18341-18345. doi: 10.1021/jacs.0c10615. Epub 2020 Oct 19.

Abstract

The ring-closing reactions based on chemical bond metathesis enable the efficient construction of a wide variety of cyclic systems which receive broad interest from medicinal and organic communities. However, the analogous reaction with C-N bond metathesis as a strategic fundamental step remains an unanswered challenge. Herein, we report the design of a new fundamental metallic C-N bond metathesis reaction that enables the palladium-catalyzed ring-closing reaction of aminodienes with aminals. The reactions proceed efficiently under mild conditions and exhibit broad substrate generality and functional group compatibility, leading to a wide variety of 5- to 16-membered N-heterocycles bearing diverse frameworks and functional groups.

Publication types

  • Research Support, Non-U.S. Gov't