Research & Teaching Faculty

Default Header Image

Catalytic and Atom-Economic C −C Bond Formation: Alkyl Tantalum Ureates for Hydroaminoalkylation

TitleCatalytic and Atom-Economic C −C Bond Formation: Alkyl Tantalum Ureates for Hydroaminoalkylation
Publication TypeJournal Article
Year of Publication2018
AuthorsDiPucchio, RC, Roşca, S-C, Schafer, LL
JournalAngewandte Chemie International Edition
Volume57
Pagination3469-3472
KeywordsAMINES, C−H activation, HYDROAMINOALKYLATION, tantalum alkyls, ureates
Abstract

Abstract Atom-economic and regioselective C −C bond formation has been achieved by rapid C−H alkylation of unprotected secondary arylamines with unactivated alkenes. The combination of Ta(CH2SiMe3)3Cl2, 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.

URLhttps://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201712668
DOI10.1002/anie.201712668