Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(7), С. 1450 - 1456
Опубликована: Янв. 1, 2023
The
Ru(dppbsa)-catalyzed
reductive
amination
of
ketones
with
nitroarenes
and
nitriles
using
H2
as
the
environmentally
benign
hydrogen
surrogate
is
developed
in
this
study.
Cross-experiments
demonstrated
that
both
reactions
are
initiated
by
reduction
or
to
corresponding
amines,
followed
condensation
give
imines
thereafter
hydrogenation.
However,
route
formation
an
amino-ligated
Ru
complex
during
nitriles,
situ
nucleophilic
C-N
coupling,
cannot
be
completely
excluded.
This
newly
versatile
method
features
good
functional
group
tolerance,
which
provides
a
novel
design
platform
for
homogeneous
catalysts
constructing
motifs
secondary
amines.
Chemical Society Reviews,
Год журнала:
2024,
Номер
53(9), С. 4607 - 4647
Опубликована: Янв. 1, 2024
This
review
collectively
discussed
the
utilisation
of
alcohols
in
various
organic
transformations
and
their
application
toward
intermediates
drugs,
drug
derivatives
natural
product-like
molecules.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(4), С. 2245 - 2259
Опубликована: Фев. 8, 2023
Catalytic
reduction
reactions
using
methanol
as
a
transfer
hydrogenating
agent
is
gaining
significant
attention
because
this
simple
alcohol
inexpensive
and
produced
on
bulk
scale.
Herein,
we
report
the
catalytic
utilization
of
hydrogen
source
for
different
functional
organic
compounds
such
nitroarenes,
olefins,
carbonyl
compounds.
The
key
to
success
transformation
use
commercially
available
Pt/C
catalyst,
which
enabled
hydrogenation
series
functionalized
nitroarenes-to-anilines,
alkenes-to-alkanes,
aldehydes-to-alcohols
both
solvent
donor.
practicability
Pt-based
protocol
showcased
by
demonstrating
catalyst
recycling
reusability
well
reaction
upscaling.
In
addition,
system
was
also
adaptable
N-methylation
N-alkylation
anilines
via
borrowing
process.
This
work
provides
flexible
approach
prepare
variety
value-added
products
from
readily
methanol,
Pt/C,
other
starting
materials.
ACS Catalysis,
Год журнала:
2023,
Номер
13(22), С. 15013 - 15053
Опубликована: Ноя. 6, 2023
Methanol
is
a
fundamental
feedstock
and
widely
used
in
the
chemical
petroleum
industries.
It
can
serve
as
C1
source
to
make
variety
of
C–C
C–N
bond
formation
dehydrogenative
coupling
products,
which
have
important
applications
natural
products
drug
discovery.
A
high
hydrogen
content
(12.5
wt%)
methanol
makes
it
an
effective
H2
donor
for
transfer
hydrogenation
various
reducible
functional
groups.
plethora
transition
metal-based
processes
been
developed
using
methanol.
Notably,
recent
review
articles
focused
on
aspect
However,
more
updated
that
examines
challenges
both
C1-source
H2-source
organic
transformations
contributing
concept
economy
has
not
presented
yet.
This
Review
summarizes
(homogeneous,
heterogeneous,
photo-)
catalyst
system
C-,
N-,
O-methylation
ketones,
alcohols,
amides,
nitriles,
heterocyclic
compounds,
sulfones,
amines,
sulfonamides
direct
N-methylation
nitro
compounds
under
borrowing
strategy
N-formylation
amines
acceptorless
dehydrogenation
source.
also
covers
insights
into
reaction
mechanisms
role
carefully
selected
ligands
metal
catalysis
activation
incorporation
-CD3,
methylation
molecules.
Moreover,
describes
groups
such
aldehydes,
alkynes,
with
detail.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(9), С. 2638 - 2664
Опубликована: Янв. 1, 2024
This
review
describes
the
recent
advances
in
different
reaction
types
and
catalytic
systems
for
construction
of
C–NAr
S–NAr
bonds
by
nitroaromatic
reductive
cross-coupling.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(13)
Опубликована: Фев. 1, 2024
Abstract
The
synthesis
of
mono‐
N
‐methylated
aliphatic
primary
amines
has
traditionally
been
challenging,
requiring
noble
metal
catalysts
and
high‐pressure
H
2
for
achieving
satisfactory
yields
selectivity.
Herein,
we
developed
an
approach
the
selective
coupling
methanol
amines,
without
hydrogen,
using
a
manganese‐based
catalyst.
Remarkably,
up
to
98
%
with
broad
substrate
scope
were
achieved
at
low
catalyst
loadings.
Notably,
due
weak
base‐catalyzed
alcoholysis
formamide
intermediates,
our
novel
protocol
not
only
obviates
addition
but
also
prevents
side
secondary
‐methylation,
supported
by
control
experiments
density
functional
theory
calculations.
Organic Letters,
Год журнала:
2024,
Номер
26(4), С. 866 - 871
Опубликована: Янв. 25, 2024
In
this
study,
we
report
a
transfer
hydrogenation
protocol
that
utilizes
borane–ammonia
(H3N–BH3)
as
the
hydrogen
source
and
commercially
available
RuCl3·xH2O
precatalyst
for
selective
aromatic
reduction
of
quinolines,
quinoxalines,
pyridines,
pyrazines,
indoles,
benzofurans,
furan
derivatives
to
form
corresponding
alicyclic
heterocycles
in
good
excellent
isolated
yields.
Applications
straightforward
include
efficient
preparation
useful
key
pharmaceutical
intermediates,
such
donepezil
flumequine,
including
biologically
active
compound.
Green Chemistry,
Год журнала:
2024,
Номер
26(6), С. 3021 - 3038
Опубликована: Янв. 1, 2024
Production
of
value-added
chemicals
from
renewable
feedstocks
is
an
attractive
platform
to
alleviate
the
shortage
petroleum
resources
and
minimize
CO
2
emissions.
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(22), С. 5028 - 5046
Опубликована: Сен. 22, 2021
Abstract
C‐methylation
is
a
vitally
important
reaction
applicable
in
chemical
synthesis
and
structure‐based
drug
design.
Notably,
the
“magic
methyl”
effect
has
become
decisive
medicinal
chemistry
discovery
for
modulation
of
bio‐active
properties
life
science
molecules.
In
this
regard,
widely
applied
modification
various
biomolecules,
pharmaceuticals,
natural
products.
general,
often
relies
on
activated,
hazardous
uneconomical
methyl
sources
such
as
diazomethane,
dimethyl
sulfate,
halides.
To
achieve
methylation
reactions
sustainable
cost‐effective
manner,
use
‘ideal’
C1
source
crucial.
methanol
constitutes
an
expedient
−CH
3
because
simple
alcohol
less‐hazardous,
inexpensive,
abundantly
available
platform
well
it
produces
only
water
by‐product
processes.
Regarding
potential
catalysts
to
perform
using
by
hydrogen
borrowing
methodology,
non‐noble
metal‐based
are
highly
preferable
due
their
unique
advantages
more
abundance,
inexpensive
low‐toxicity.
recent
years,
chemists
made
significant
contributions
towards
catalytic
valorization
insert
groups
via
C−H
activation
variety
compounds
Consequently,
minireview
we
summarize
process
applying
Fe‐,
Mn‐,
Co‐
Ni‐based
metal
free
catalysts.
magnified
image
