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Updated: Jun 23, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Efficient carbene transfer reactivity mediated by Fe(II) complexes supported by bulky alkoxides
Lakshani W Kulathungage1, Sudheer S Kurup1, Edison A Browne2
1Department of Chemistry, Wayne State University, 5101 Cass Ave., Detroit, MI 48202, USA. groysman@chem.wayne.edu.
Abstract:
Herein we describe the stoichiometric and catalytic carbene-transfer reactivity of iron(II) alkoxide complexes with iodonium ylide precursors. Treatment of PhIC(CO2Me)2 with styrene in the presence of catalytic amounts of several different Fe(OR)2(THF)2 precursors results in efficient cyclopropanation for a variety of styrenes. Computational and reactivity studies suggest a novel remote metallocarbene/vinyl radical intermediate, Fe(OR)2(κ2-(OC(OMe))2C), which could be responsible for the reactive nature of the catalyst.
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