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Copper Acetoacetonate [Cu(acac) 2 ]/BINAP‐Promoted C sp 3 N Bond Formation via Reductive Coupling of N ‐Tosylhydrazones with Anilines
Author(s) -
Aziz Jessy,
Brion JeanDaniel,
Hamze Abdallah,
Alami Mouad
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300466
Subject(s) - chemistry , copper , reagent , binap , reductive amination , chemoselectivity , stoichiometry , hydride , coupling reaction , combinatorial chemistry , medicinal chemistry , metal , catalysis , organic chemistry , enantioselective synthesis
We report the the copper(II) acetoacetonate [Cu(acac) 2 ]/BINAP‐catalyzed synthesis of arylamines from N ‐tosylhydrazones and anilines. A fine tuning of the reaction conditions was required to accomplish the cross‐coupling successfully, including the ligands effect and the addition of small amounts of water. The characteristic feature of this protocol is its functional group compatibility and its chemoselectivity when various aminophenol derivatives were used. Taking into consideration the interest for this copper‐reductive coupling in which no stoichiometric metal hydride reagent is employed, this can be considered as an alternative to the conventional reductive amination.