title: d-Glucose: An Efficient Reducing Agent for a Copper(II)-Mediated Arylation of Primary Amines in Water.
abstract: A copper-catalyzed Ullmann-type amination with primary amines in water with a combination of copper(II) triflate [Cu(OTf)2], dipivaloylmethane, and d-glucose is reported. The mild conditions and the use of an inexpensive catalyst as well as a renewable feedstock (d-glucose and the surfactant TPGS-750-M, which is derived from vitamin E) make this protocol a safe and convenient strategy for efficient C-N bond formation. This easy-to-handle procedure is extremely competitive compared to palladium-based reactions and may be used to synthesize N-containing molecules, such as drugs or organic light-emitting diodes (OLEDs).
authors: Laboratoire d'Innovation Thérapeutique, University of Strasbourg, 74 route du Rhin, BP60024, 67401, Illkirch, France.
authors: Maud
authors: M
authors: Bollenbach
authors: Laboratoire d'Innovation Thérapeutique, University of Strasbourg, 74 route du Rhin, BP60024, 67401, Illkirch, France.
authors: Patrick
authors: P
authors: Wagner
authors: Laboratoire d'Innovation Thérapeutique, University of Strasbourg, 74 route du Rhin, BP60024, 67401, Illkirch, France.|Laboratório de Pesquisa em Recursos Naturais, Universidade Federal de Alagoas, Maceió, AL, Brazil.
authors: Pedro G V
authors: PG
authors: Aquino
authors: Laboratoire d'Innovation Thérapeutique, University of Strasbourg, 74 route du Rhin, BP60024, 67401, Illkirch, France.
authors: Jean-Jacques
authors: JJ
authors: Bourguignon
authors: Laboratoire d'Innovation Thérapeutique, University of Strasbourg, 74 route du Rhin, BP60024, 67401, Illkirch, France.
authors: Frédéric
authors: F
authors: Bihel
authors: Laboratoire d'Innovation Thérapeutique, University of Strasbourg, 74 route du Rhin, BP60024, 67401, Illkirch, France.|SpiroChem AG, c/o ETH-Zürich, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
authors: Christophe
authors: C
authors: Salomé
authors: Laboratoire d'Innovation Thérapeutique, University of Strasbourg, 74 route du Rhin, BP60024, 67401, Illkirch, France.
authors: Martine
authors: M
authors: Schmitt
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry*; D019163:Reducing Agents / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D000588:Amines; D019163:Reducing Agents; D014867:Water; D003300:Copper; D005947:Glucose
keywords: amination; amines; carbohydrates; copper; micelles