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Updated: Oct 9, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Copper-Catalyzed Conjugate Additions to Isocyanoalkenes
John-Paul R Marrazzo1, Allen Chao2, Yajun Li3
1Department of Chemistry, Drexel University, 3401 Chestnut Street, Philadelphia, Pennsylvania 19104-2875, United States.
Abstract:
A copper iodide-Pyox complex catalyzes the first conjugate addition of diverse sulfur, nitrogen, and carbon nucleophiles to isocyanoalkenes. The anionic addition generates metalated isocyanoalkanes capable of SNi displacements, providing a rapid route to a series of functionalized, cyclic isocyanoalkanes. The Cu(I)I-Pyox complex efficiently catalyzes a first-in-class conjugate addition affording a range of complex, functionalized isocyanoalkanes that are otherwise challenging to synthesize while laying a foundation for catalytic reactions that maintain the isocyanide group.
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