Halogen-Bond-Induced Consecutive C sp3-H Aminations via Hydrogen Atom Transfer Relay Strategy

Org Lett. 2020 Mar 20;22(6):2135-2140. doi: 10.1021/acs.orglett.0c00081. Epub 2020 Feb 28.

Abstract

The utilization of a halogen bond in a number of chemical fields is well-known. Surprisingly, the incorporation of this useful noncovalent interaction in chemical reaction engineering is rare. We disclose here an uncommon use of halogen bonding to induce intermolecular Csp3-H amination while enabling a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions at distinct reaction stages.

Publication types

  • Research Support, Non-U.S. Gov't