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Published on: February 7, 2019
Bicyclo[1.1.0]butane Carboxamides to N-Heterocycles via a Strain Release-Enabled Nickel(II)-Carbene Intermediate
Akanksha Babbar1, Braj Gopal1, Dongari Yadagiri1
1Laboratory of Organic Synthesis and Catalysis, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand247667, India.
Abstract:
We report the conversion of bicyclo[1.1.0]butane carboxamides into N-heterocycles via strain release, enabling the generation of a novel class of Ni(II)-carbene intermediate and utilizing it for Ni(II)-carbene alkyne metathesis reactions for cyclopropanation and [4+2] cycloaddition to access highly functionalized cyclopropane-containing tetracyclic quinolinones and phenanthridinones. This transformation exhibits a broad scope and high yields across diverse substrates, with mechanistic studies confirming the formation of Ni(II)-carbene via a trapping experiment. Synthetic utility was demonstrated, and bioactive molecules were incorporated into the N-heterocyclic core.
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