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Updated: Jun 6, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Electron Donor-Acceptor Complex-Driven Divergent Routes to α-Amino Bicyclopentyl Iodides and Methylene Cyclobutanols
Vinjamuri Srinivasu1, Koustav Pal1, Shirshendu Giri1
1Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur 741246, West Bengal, India.
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-amino-functionalized 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 Cs2CO3, 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.
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