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Thomas TJ, Merritt BA, Lemma BE, et al. Cyclopropenation of internal alkynylsilanes and diazoacetates catalyzed by copper(i) N-heterocyclic carbene complexes. Org Biomol Chem. 2016;14(5):1742-7doi: 10.1039/c5ob02259b.
Thomas, T. J., Merritt, B. A., Lemma, B. E., McKoy, A. M., Nguyen, T., Swenson, A. K., Mills, J. L., & Coleman, M. G. (2016). Cyclopropenation of internal alkynylsilanes and diazoacetates catalyzed by copper(i) N-heterocyclic carbene complexes. Organic & biomolecular chemistry, 14(5), 1742-7. https://doi.org/10.1039/c5ob02259b
Thomas, Thomas J, et al. "Cyclopropenation of internal alkynylsilanes and diazoacetates catalyzed by copper(i) N-heterocyclic carbene complexes." Organic & biomolecular chemistry vol. 14,5 (2016): 1742-7. doi: https://doi.org/10.1039/c5ob02259b
Thomas TJ, Merritt BA, Lemma BE, McKoy AM, Nguyen T, Swenson AK, Mills JL, Coleman MG. Cyclopropenation of internal alkynylsilanes and diazoacetates catalyzed by copper(i) N-heterocyclic carbene complexes. Org Biomol Chem. 2016 Feb 07;14(5):1742-7. doi: 10.1039/c5ob02259b. PMID: 26739570.
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Org Biomol Chem. 2016 Feb 07;14(5):1742-7. doi: 10.1039/c5ob02259b.

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

Organic & biomolecular chemistry

Thomas J Thomas, Benjamin A Merritt, Betsegaw E Lemma, Adina M McKoy, Tri Nguyen, Andrew K Swenson, Jeffrey L Mills, Michael G Coleman

Affiliations

  1. School of Chemistry and Materials Science, Rochester Institute of Technology, Rochester, NY 14623, USA. [email protected].

PMID: 26739570 DOI: 10.1039/c5ob02259b

Abstract

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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