Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 5, Pages 1742-1747Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob02259b
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Funding
- Rochester Institute of Technology (RIT) FEAD grant
- RIT Office of the Vice President of Research
- RIT Honor's program
- RIT SCMS
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Copper(I) N-heterocyclic carbene (CuNHC) complexes are more catalytically active than traditional transition metal salts for the cyclopropenation of internal alkynylsilanes and diazoacetate compounds. A series of 1,2,3-trisubstituted and 1,2,3,3-tetrasubstituted cyclopropenylsilane compounds were isolated in good overall yields. An interesting regioselective and chemodivergent reaction pathway was also observed to furnish a tetra-substituted furan for an electron-rich donor/acceptor diazoacetate. Finally, a practical synthesis of a cyclopropenyl-containing starting material that is useful for bioorthogonal chemistry is also described.
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