Cyclopropenation of internal alkynylsilanes and diazoacetates catalyzed by copper(i) N-heterocyclic carbene complexes
| Autor: | Andrew K. Swenson, Michael G. Coleman, Benjamin A. Merritt, Tri Nguyen, Adina M. McKoy, Jeffrey Mills, Betsegaw E. Lemma, Thomas J. Thomas |
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| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Chemistry Organic Chemistry chemistry.chemical_element Regioselectivity Nanotechnology 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Copper Acceptor 0104 chemical sciences Catalysis chemistry.chemical_compound Transition metal Furan Physical and Theoretical Chemistry Bioorthogonal chemistry Carbene |
| Zdroj: | Organicbiomolecular chemistry. 14(5) |
| ISSN: | 1477-0539 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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