Electron Donor–Acceptor Complex-Driven Divergent Routes to α-Amino Bicyclopentyl Iodides and Methylene Cyclobutanols

Abstract

Amines are essential due to their structural diversity and biological significance. Introducing the valuable bicyclopentane (BCP) moiety at the α-position of amines offers a promising strategy for developing novel bioactive compounds. This study outlines a divergent synthesis approach to generate α-aminofunctionalized bicyclopentyl iodides and methylene cyclobutanols under mild and environmentally sustainable conditions. By employing an electron donor−acceptor (EDA) complex between amine and the inexpensive and readily available inorganic base Cs 2 CO 3 , this method circumvents the need for strongly reducing, metal-based photocatalysts typically required for aryl radical generation. This approach enables the α-functionalization of various aliphatic and alicyclic amines via a 1,5-hydrogen atom transfer mechanism.