European Journal of Organic Chemistry,
Год журнала:
2021,
Номер
2021(43), С. 5862 - 5879
Опубликована: Окт. 20, 2021
Abstract
Maleimides
and
succinimides
are
all
vital
scaffolds
in
biological
fields
various
natural
products.
Maleimide
derivatives
have
been
extensively
used
as
coupling
partners
for
organic
transformations,
affording
a
broad
array
of
important
molecular
architectures
including
succinimides.
In
the
past
decade,
variety
efficient
chelation‐assisted
strategies
employed
selective
addition
C−H
bonds
to
maleimides
giving
succinimides,
which
also
highly
building
blocks
synthesis.
This
Review
provides
an
overview
research
progress
relating
participated
transition‐metal‐catalyzed
group‐directed
alkylation
from
2012
2021.
Significant
advances
this
field
were
highlighted,
diverse
transition
metal
catalysts,
substrates
contained
different
directing
groups,
reaction
mechanisms
well
synthetic
applications
systematically
discussed.
addition,
limitations
intractable
issues
need
be
solved
future
pointed
out.
Chemical Reviews,
Год журнала:
2023,
Номер
123(12), С. 7692 - 7760
Опубликована: Май 10, 2023
Site-predictable
and
chemoselective
C–H
bond
functionalization
reactions
offer
synthetically
powerful
strategies
for
the
step-economic
diversification
of
both
feedstock
fine
chemicals.
Many
transition-metal-catalyzed
methods
have
emerged
selective
activation
bonds.
However,
challenges
regio-
chemoselectivity
with
application
to
highly
complex
molecules
bearing
significant
functional
group
density
diversity.
As
molecular
complexity
increases
within
structures
risks
catalyst
intolerance
limited
applicability
grow
number
groups
potentially
Lewis
basic
heteroatoms.
Given
abundance
bonds
already
diversified
such
as
pharmaceuticals,
natural
products,
materials,
design
selection
reaction
conditions
tolerant
catalysts
has
proved
critical
successful
direct
functionalization.
such,
innovations
formation
carbon–carbon
been
discovered
developed
overcome
these
limitations.
This
review
highlights
progress
made
metal-catalyzed
C–C
forming
including
alkylation,
methylation,
arylation,
olefination
targets.
Nature Communications,
Год журнала:
2019,
Номер
10(1)
Опубликована: Сен. 11, 2019
Abstract
The
development
of
intermolecular
alkene
aminopyridylation
has
great
potential
for
quickly
increasing
molecular
complexity
with
two
valuable
groups.
Here
we
report
a
strategy
the
photocatalytic
alkenes
using
variety
N-aminopyridinium
salts
as
both
aminating
and
pyridylating
reagents.
Using
Eosin
Y
photocatalyst,
amino
pyridyl
groups
are
simultaneously
incorporated
into
alkenes,
affording
synthetically
useful
aminoethyl
pyridine
derivatives
under
mild
reaction
conditions.
Remarkably,
C4-regioselectivity
in
radical
trapping
salt
can
be
controlled
by
electrostatic
interaction
between
pyridinium
nitrogen
sulfonyl
group
β-amino
radical.
This
transformation
is
characterized
broad
substrate
scope,
good
functional
compatibility,
utility
this
was
further
demonstrated
late-stage
functionalization
complex
biorelevant
molecules.
Combining
experiments
DFT
calculations
on
mechanism
investigated
to
propose
complete
regioselectivity.
Journal of the American Chemical Society,
Год журнала:
2021,
Номер
143(21), С. 7909 - 7914
Опубликована: Май 24, 2021
Herein,
we
present
an
undirected
para-selective
two-step
C–H
alkylation
of
complex
arenes
useful
for
late-stage
functionalization.
The
combination
a
site-selective
thianthrenation
with
palladium-catalyzed
reductive
electrophile
cross-coupling
grants
access
to
diverse
range
synthetically
alkylated
which
cannot
be
accessed
otherwise
comparable
selectivity,
diversity,
and
practicality.
robustness
this
transformation
is
further
demonstrated
by
thianthrenium-based
coupling
two
fragments.
Chemistry - A European Journal,
Год журнала:
2019,
Номер
26(2), С. 369 - 373
Опубликована: Окт. 9, 2019
A
practical
and
scalable
protocol
for
visible-light-accelerated
arylation
alkylation
of
quinoxalin-2(1H)-ones
with
hydrazines
is
reported.
In
this
protocol,
a
hydrazone-based
two-dimensional
covalent
organic
frameworks
(2D-COF-1)
was
employed
as
the
heterogeneous
photocatalyst
(PC).
Due
to
its
excellent
photocatalytic
properties,
good
chemical
stability
nature,
present
method
exhibits
high
efficiency,
functional
group
tolerance,
easy
scalability
remarkable
catalyst
reusability.
More
importantly,
it
provides
an
alternative
way
that
allows
rapid
access
various
C3
arylated
or
alkylated
in
greener
sustainable
manner.
Angewandte Chemie International Edition,
Год журнала:
2020,
Номер
60(12), С. 6660 - 6666
Опубликована: Окт. 8, 2020
The
mechanochemical,
solvent-free,
highly
regioselective,
rhodium-catalyzed
C-H
methylation
of
(hetero)arenes
is
reported.
reaction
shows
excellent
functional-group
compatibility
and
demonstrated
to
work
for
the
late-stage
biologically
active
compounds.
method
requires
no
external
heating
benefits
from
considerably
shorter
times
than
previous
solution-based
protocols.
Additionally,
mechanochemical
approach
shown
enable
efficient
synthesis
organometallic
complexes
that
are
difficult
generate
conventionally.
Beilstein Journal of Organic Chemistry,
Год журнала:
2020,
Номер
16, С. 1754 - 1804
Опубликована: Июль 21, 2020
While
aiming
at
sustainable
organic
synthesis,
over
the
last
decade
particular
attention
has
been
focused
on
two
modern
fields,
C-H
bond
activation,
and
visible-light-induced
photocatalysis.
Couplings
through
activation
involve
use
of
non-prefunctionalized
substrates
that
are
directly
converted
into
more
complex
molecules,
without
need
a
previous
functionalization,
thus
considerably
reduce
waste
generation
number
synthetic
steps.
In
parallel,
transformations
involving
photoredox
catalysis
promote
radical
reactions
in
absence
initiators.
They
conducted
under
particularly
mild
conditions
while
using
visible
light
as
cheap
economic
energy
source.
this
way,
these
strategies
follow
requirements
environment-friendly
chemistry.
Regarding
intrinsic
advantages
well
complementary
mode
action
catalytic
previously
introduced,
their
merging
synergistic
dual
system
is
extremely
appealing.
perspective,
scope
review
aims
to
present
innovative
combining
visible-light
induced
ACS Catalysis,
Год журнала:
2021,
Номер
11(6), С. 3268 - 3292
Опубликована: Март 1, 2021
Alkylation
represents
an
important
organic
transformation
in
molecular
science
to
develop
privileged
alkylated
arenes
and
heteroarenes.
Especially,
the
direct
C–H
bond
alkylation
using
unactivated
alkyl
halides
is
a
straightforward
attractive
approach
from
both
step-economy
chemoselectivity
perspectives.
Substantial
progress
has
been
made
primary,
secondary,
tertiary
along
with
methylation
fluoroalkylation.
This
Review
broadly
summarizes
transition-metal-catalyzed
alkylations
of
bonds
on
various
heteroarenes
until
October
2020.
On
basis
substrates
utilized
for
alkylation,
divided
into
two
major
sections:
ACS Catalysis,
Год журнала:
2022,
Номер
12(4), С. 2330 - 2347
Опубликована: Фев. 1, 2022
Transition-metal-catalyzed
alkylation
of
(hetero)arenes
with
three-membered
carbo-/heterocycles
involving
C–H
activation
and
ring
scission
has
been
greatly
developed
over
the
past
few
years.
The
chelation-assisted
strategies
for
controlling
reactivity
site
selectivity
in
these
protocols
include
use
nitrogen-containing
directing
groups,
pre-existing
functional
a
Catellani-type
intermediate,
thereby
providing
rapid
access
to
numerous
oxygen-
or
heterocyclic
systems.
This
review
gives
an
update
area
various
catalytic
methodologies
applications
total
synthesis
natural
products
rings
as
alkylating
reagents,
which
are
classified
into
following
three
categories
on
basis
employed
strategies:
(i)
directed
by
(ii)
(iii)
aryl-NBE
intermediates
(Catellani-type
cascade
reaction).
