d-Glucose: An Efficient Reducing Agent for a Copper(II)-Mediated Arylation of Primary Amines in Water

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). A spoonful of sugar: A low‐temperature Ullmann‐type reaction under micellar conditions in water is developed for the coupling of primary aliphatic amines. The use of renewable feedstocks (d‐glucose and the surfactant TPGS‐750‐M, which is composed of vitamin E), the absence of organic solvent, and the economy of energy make these conditions environmentally friendly and adaptable to industrial production.