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Catalytic and Atom‐Economic C sp 3 −C sp 3 Bond Formation: Alkyl Tantalum Ureates for Hydroaminoalkylation
Author(s) -
DiPucchio Rebecca C.,
Roşca SorinClaudiu,
Schafer Laurel L.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201712668
Subject(s) - alkene , chemistry , alkylation , catalysis , regioselectivity , alkyl , aniline , medicinal chemistry , amine gas treating , ligand (biochemistry) , oxidative addition , polymer chemistry , organic chemistry , biochemistry , receptor
Atom‐economic and regioselective Csp3−Csp3bond formation has been achieved by rapid C−H alkylation of unprotected secondary arylamines with unactivated alkenes. The combination of Ta(CH 2 SiMe 3 ) 3 Cl 2 , and a ureate N , O ‐chelating‐ligand salt gives catalytic systems prepared in situ that can realize high yields of β‐alkylated aniline derivatives from either terminal or internal alkene substrates. These new catalyst systems realize C−H alkylation in as little as one hour and for the first time a 1:1 stoichiometry of alkene and amine substrates results in high yielding syntheses of isolated amine products by simple filtration and concentration.