Zn2+ templating enables synthesis of redox ‘non-innocent’ diimine pyridine ligands with strong electron-withdrawing groups, allowing construction of iron complexes with multiple ligand-based reductions for application in redox flow batteries.
Ni(II) complexes supported by tridentate N^N − ^N diarylamido pincer-type ligands have been demonstrated to act as active catalysts in the carbon−carbon bond forming alkylation of azoles using unactivated alkyl halides. Here, we show that benzannulated phenanthridine-containing ligands can form homogeneous Ni(II) catalysts active with both benzoxazole and benzothiazole substrates. These precatalysts have been fully characterized in solution and the solid state, including by cyclic voltammetry.
The direct electrochemical hydrogenation of unsaturated organic compounds containing C=N and C=O bonds using glassy carbon electrodes and widely available Brønsted acids is demonstrated for a selection of α-ketoesters and...
The Pd-catalyzed Buchwald–Hartwig
amination of 2-bromo-1-iodobenzene
with (4-amino-2-tert-butyl)phenanthridine using 1,1′-bis(diphenylphosphino)ferrocene
(dppf) results in a side reaction involving the first reported example
of P–C bond activation of dppf and the templated formation
of an N∧N–∧P-supported
Pd(II) coordination complex. The full characterization of this complex
along with a proposed mechanism for a rare example of unstrained P–C(cyclopentadienyl)
bond activation are described.
The synthesis and full characterization
of a series of ferrocene-decorated
pyrimidines with donor-acceptor-donor (D-A-D) and donor-acceptor-acceptor
(D-A-A) architectures are reported. The three novel compounds share
a pyrimidine core and single ferrocenyl donor arm, with an additional
substituent varied from donor ferrocene (1) to acceptor
pyrenyl (2) to donor (4-diphenylamino)phenyl groups (3). The compounds could be easily constructed in acceptable
yields in one-pot reactions via acceptorless dehydrogenative coupling
reactions mediated by a ruthenium coordination complex supported by
a simple bidentate P^N ligand. The solution and solid-state
structures of the new pyrimidines are described along with photophysical
and computational characterization. The lack of near IR (NIR) transitions
upon single-electron oxidation of the compounds implies that the pyrimidinyl
unit is less effective at mediating electronic communication compared
with pyridine or pyrrole cores. Nevertheless, strong absorption in
the far visible and NIR is observed upon formation of a dicationic
species from 3 and is attributed to efficient charge
transfer from the pyrimidine core to the oxidized donor units.
The synthesis of a series of 2- and 8-substituted 4-amino-7-chloroquinolines is presented. The chloro in the 7-position can be effectively substituted using amino alcohols to yield novel analogues of the antimalarial (hydroxy)chloroquine. Both short chain (2-aminoethanol) and long chain (5-[N-ethyl-N-(2-hydroxyethyl)amino]-2-aminopentane) coupling partners can be used. While ketone and nitro functionalities were found to be incompatible with the coupling conditions, electron-donating amino and dimethylamino substituents were tolerated. In addition to characterization in solution using multinuclear NMR spectroscopy and high-resolution mass spectrometry, single-crystal X-ray structures are presented of two 4,7-dichloroquinolines as well as three of the N-alkylated products including a unique species in which a pyrrole heterocycle formed at the 2-position of the quinoline sub-unit and a rare example of a 4-aza-1,10-phenanthroline.
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