10.1021/om400906u.s001
Arup Mukherjee
Arup
Mukherjee
Tamal K. Sen
Tamal K.
Sen
Pradip Kr. Ghorai
Pradip Kr.
Ghorai
Swadhin K. Mandal
Swadhin K.
Mandal
Organozinc Catalyst on a Phenalenyl Scaffold for Intramolecular
Hydroamination of Aminoalkenes
American Chemical Society
2013
Phenalenyl Scaffold
organozinc compound 2
cation
HN
catalyst 2
Intramolecular Hydroamination
ligand
ZnMe 2
intramolecular hydroamination
Organozinc Catalyst
NMR spectroscopy
AminoalkenesThe syntheses
hydroamination reaction
DFT calculation
PLY
ZnMe 2. Reactions
organozinc compounds
2013-12-09 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Organozinc_Catalyst_on_a_Phenalenyl_Scaffold_for_Intramolecular_Hydroamination_of_Aminoalkenes/2345545
The
syntheses and characterization of two organozinc compounds were accomplished
by reacting phenalenyl (PLY)-based ligands with ZnMe<sub>2</sub>.
Reactions of [HN(Cy),O-PLY] and [HN(Cy),N(Cy)-PLY] ligands with ZnMe<sub>2</sub> led to the formation of the dimeric orange-colored organozinc
compound [N(Cy),O-PLY-ZnMe]<sub>2</sub> (<b>1</b>) and red-colored
monomeric organozinc compound [N(Cy),N(Cy)-PLY-ZnMe] (<b>2</b>) under evolution of methane. Both <b>1</b> and <b>2</b> were characterized by NMR spectroscopy, elemental analysis, and
single-crystal X-ray diffraction study. The organozinc compound <b>2</b> was tested as a catalyst for intramolecular hydroamination
of both unactivated primary and secondary aminoalkenes in the presence
of an externally added activator, which generated the zinc-based cation <i>in situ</i>. The catalytic result obtained from the present
catalyst <b>2</b> was compared with the catalysts having similar
structure from previous studies. The DFT calculation indicates that
the stability of the <i>in situ</i> generated cation plays
a significant role in the catalytic activity in the hydroamination
reaction.