Intermolecular Redox-Neutral Amine C-H Functionalization Induced by the Strong Boron Lewis Acid B(C6F5)3in the Frustrated Lewis Pair Regime.
N,N-Dimethylmesitylamine undergoes an intermolecular redox-neutral C-H activation/C-C coupling process upon treatment with dimethyl acetylenedicarboxylate and the strong boron Lewis acid B(C6F5)3. Similarly, N,N-dimethylmesitylamine reacts with two molar equivalents of ethyl acrylate to give the respective unsaturated coupling product with H2transfer to the acrylic ester to form the ethyl propionate/B(C6F5)3adduct. N,N-Dimethylmesitylamine also undergoes a C-H activation at the benzylic ortho sp3-carbon atom with dihydrogen formation upon treatment with Piers' borane [HB(C6F5)2]. The last two reactions of N,N-dimethylmesitylamine were analyzed by DFT calculations.
Organisch-Chemisches Institut der, Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
Guo-Qiang
GQ
Chen
Organisch-Chemisches Institut der, Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
Gerald
http://orcid.org/0000-0002-5196-2491
G
Kehr
Organisch-Chemisches Institut der, Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
Constantin G
CG
Daniliuc
Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn, Beringstraße 4, 53115, Bonn, Germany.
Markus
http://orcid.org/0000-0001-6711-5804
M
Bursch
Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn, Beringstraße 4, 53115, Bonn, Germany.
Stefan
S
Grimme
Organisch-Chemisches Institut der, Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
Gerhard
http://orcid.org/0000-0003-2488-3699
G
Erker
C−C coupling; C−H activation; boron; hydride transfer; nitrogen