title: An Exclusively trans-Selective Chlorocarbamoylation of Alkynes Enabled by a Palladium/Phosphaadamantane Catalyst.
abstract: Pharmaceutically relevant methylene oxindoles are synthesized by a palladium(0)-catalyzed intramolecular chlorocarbamoylation reaction of alkynes. A relatively underexplored class of caged phosphine ligands is uniquely suited for this transformation, enabling high levels of reactivity and exquisite trans selectivity. This report entails the first transition-metal-catalyzed atom-economic addition of a carbamoyl chloride across an alkyne.
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario M5S 3H6 (Canada).
authors.forename: Christine M
authors.initials: CM
authors.lastname: Le
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario M5S 3H6 (Canada).
authors.forename: Xiao
authors.initials: X
authors.lastname: Hou
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany).
authors.forename: Theresa
authors.initials: T
authors.lastname: Sperger
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany). franziska.schoenebeck@rwth-aachen.de.
authors.forename: Franziska
authors.initials: F
authors.lastname: Schoenebeck
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario M5S 3H6 (Canada). mlautens@chem.utoronto.ca.
authors.forename: Mark
authors.initials: M
authors.lastname: Lautens
keywords: chlorocarbamoylation; cyclization; homogenous catalysis; palladium; phosphaadamantane