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d ‐Glucose: An Efficient Reducing Agent for a Copper(II)‐Mediated Arylation of Primary Amines in Water
Author(s) -
Bollenbach Maud,
Wagner Patrick,
Aquino Pedro G. V.,
Bourguig JeanJacques,
Bihel Frédéric,
Salomé Christophe,
Schmitt Martine
Publication year - 2016
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201600801
Subject(s) - amination , chemistry , copper , catalysis , trifluoromethanesulfonate , combinatorial chemistry , palladium , primary (astronomy) , reductive amination , organic chemistry , physics , astronomy
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).