Cyclopropenation of internal alkynylsilanes and diazoacetates catalyzed by copper(i) N-heterocyclic carbene complexes

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 is...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-02, Vol.14 (5), p.1742-1747
Main Authors: Thomas, Thomas J, Merritt, Benjamin A, Lemma, Betsegaw E, McKoy, Adina M, Nguyen, Tri, Swenson, Andrew K, Mills, Jeffrey L, Coleman, Michael G
Format: Article
Language:English
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob02259b