title: Cyclopropenation of internal alkynylsilanes and diazoacetates catalyzed by copper(i) N-heterocyclic carbene complexes.
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.
authors.affiliation: School of Chemistry and Materials Science, Rochester Institute of Technology, Rochester, NY 14623, USA. mgcsch@rit.edu.
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Thomas
authors.affiliation: School of Chemistry and Materials Science, Rochester Institute of Technology, Rochester, NY 14623, USA. mgcsch@rit.edu.
authors.forename: Benjamin A
authors.initials: BA
authors.lastname: Merritt
authors.affiliation: School of Chemistry and Materials Science, Rochester Institute of Technology, Rochester, NY 14623, USA. mgcsch@rit.edu.
authors.forename: Betsegaw E
authors.initials: BE
authors.lastname: Lemma
authors.affiliation: School of Chemistry and Materials Science, Rochester Institute of Technology, Rochester, NY 14623, USA. mgcsch@rit.edu.
authors.forename: Adina M
authors.initials: AM
authors.lastname: McKoy
authors.affiliation: School of Chemistry and Materials Science, Rochester Institute of Technology, Rochester, NY 14623, USA. mgcsch@rit.edu.
authors.forename: Tri
authors.initials: T
authors.lastname: Nguyen
authors.affiliation: School of Chemistry and Materials Science, Rochester Institute of Technology, Rochester, NY 14623, USA. mgcsch@rit.edu.
authors.forename: Andrew K
authors.initials: AK
authors.lastname: Swenson
authors.affiliation: School of Chemistry and Materials Science, Rochester Institute of Technology, Rochester, NY 14623, USA. mgcsch@rit.edu.
authors.forename: Jeffrey L
authors.initials: JL
authors.lastname: Mills
authors.affiliation: School of Chemistry and Materials Science, Rochester Institute of Technology, Rochester, NY 14623, USA. mgcsch@rit.edu.
authors.forename: Michael G
authors.initials: MG
authors.lastname: Coleman