<scp>d</scp>‐Glucose: An Efficient Reducing Agent for a Copper(II)‐Mediated Arylation of Primary Amines in Water

Maud Bollenbach, Patrick Wagner, Pedro Gregório Vieira Aquino, Jean‐Jacques Bourguignon, Frédéric Bihel, Christophe Salomé, Martine Schmitt

ChemSusChem · 2016 · 35 citations · 47 references

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Abstract

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).

References

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