Chinese Journal of Organic Chemistry,
Год журнала:
2023,
Номер
43(8), С. 2591 - 2591
Опубликована: Янв. 1, 2023
In
recent
years,
the
photochemical
organic
transformation
promoted
by
visible
light
has
aroused
interest
of
chemists.Compared
with
traditional
methods,
photoredox
catalysis
using
as
renewable
energy
been
proved
to
be
a
mild
and
powerful
tool,
which
can
promote
activation
molecules
single
electron
transfer
(SET)
process.There
are
lot
amino
functional
groups
in
structures
many
natural
products,
also
important
structural
units
some
drug
materials.Therefore,
activating
C-N
bond
these
substances
carrying
out
coupling
reactions
C-C
formation,
structure
compounds
effectively
modified,
so
obtain
various
functionalization.Therefore,
this
study
become
an
research
field
synthesis.The
results
breaking
its
application
formation
reaction
years
reviewed,
representative
examples
mechanisms
discussed.
Accounts of Chemical Research,
Год журнала:
2023,
Номер
56(16), С. 2170 - 2184
Опубликована: Июль 28, 2023
ConspectusSynthetic
chemists
have
consistently
aimed
to
develop
efficient
methods
for
synthesizing
ketones,
which
are
essential
building
blocks
in
organic
chemistry
and
play
significant
roles
bioactive
molecules.
Recent
efforts
focused
on
using
photoredox
catalysis,
enables
previously
inaccessible
activation
modes,
synthesize
ketones
through
the
cross-coupling
of
an
acyl
electrophile
simple
C(sp3)-H
bonds.
Over
past
few
years,
we
worked
developing
effective
versatile
approaches
directly
acylating
activated
hydrocarbons
forge
ketones.Initially,
thioesters
were
explored
as
source
achieve
direct
acylation
ethers,
but
unexpected
thioesterification
reaction
was
observed
instead.
To
gain
insights
into
this
reactivity,
conducted
optimization
conditions,
substrate
scope
evaluation,
mechanistic
studies.
Drawing
from
our
understanding
Ni/Ir
photocatalysis
obtained
study,
subsequently
developed
a
method
hydrocarbons.
The
use
less-reactive
amides
electrophiles
found
be
critical
suppressing
undesired
pathways.
This
seemingly
counterintuitive
reactivity
carefully
studied,
revealing
substrate-assisted
mechanism
suppressed
oxidative
addition
leads
early-stage
nickel
oxidation
C-H
activation.To
address
drawbacks
method,
primarily
arose
decarbonylative
transmetallative
side
pathways,
employed
N-acyllutidiniums
electrophile.
prevented
decomposition
enabling
α-chiral
substrates
with
retention
their
stereochemistry,
particularly
those
derived
α-amino
acids.
methodology
allowed
us
access
diverse
range
homologues.Despite
elegant
utility
Ni/photoredox
catalysis
new
synthetic
methodologies,
precise
behavior
catalysts
under
redox
conditions
is
incompletely
understood.
insight
chemical
reactions,
used
combination
experimental
computational
methods.
Our
investigations
revealed
that
devised
adjustments
nickel/photoredox
can
result
differences
outcomes,
providing
opportunities
tailor
reactions
designed
strategies.
We
believe
continued
study
apply
modulation
will
lead
discovery
additional
transformations.
Organic Letters,
Год журнала:
2024,
Номер
26(10), С. 2114 - 2118
Опубликована: Март 4, 2024
Herein,
we
report
a
general
and
practical
nickel-catalyzed
deaminative
alkylation
of
Katritzky
salts
with
cyclopropyl
alcohols
via
merging
C–N
C–C
bond
activation.
This
protocol
enables
the
formation
an
alkyl–alkyl
along
generation
versatile
ketone
functional
group
in
single
operation,
thus
providing
convenient
approach
for
accessing
β-alkyl
ketones.
reaction
is
distinguished
by
its
high
tolerance,
broad
substrate
scope,
efficient
late-stage
derivatization
complex
bioactive
molecules.
ACS Catalysis,
Год журнала:
2023,
Номер
14(1), С. 522 - 532
Опубликована: Дек. 22, 2023
Herein,
we
present
the
example
of
Cu-catalyzed
oxidation
coupling
amino
acids/peptides
for
producing
α-alkylated
unnatural
glycine
derivatives
by
activation
double
C(sp3)–H/C(sp3)–H
bonds.
It
is
worth
mentioning
that
tractable
conditions
and
good
functional
group
tolerance
allow
specific
site-modification
polypeptides
utilizing
this
strategy.
The
practicality
transformation
certified
potent
preparation
a
series
HDAC
inhibitors
(SPACAs),
which
performed
well
in
preliminary
biological
evaluations.
A
radical–radical
pathway
was
involved
reaction
based
on
mechanistic
studies.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(7), С. 4422 - 4433
Опубликована: Март 17, 2023
The
development
of
excited-state
palladium-catalyzed
alkylative
cyclization
acrylamides
and
the
alkylation
quinoxalinones
is
described.
application
a
variety
primary,
secondary,
tertiary
unactivated
alkyl
halides
as
radical
precursors
use
simple
catalyst
system
are
highlights
this
reactivity
manifold.
reactions
exhibit
wide
scope,
occur
under
mild
conditions,
furnish
products
in
excellent
yields.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(21), С. 14580 - 14587
Опубликована: Окт. 7, 2022
Described
is
a
mild
method
that
merges
organophotoredox
catalysis
with
hydrogen
atom
transfer
to
enable
C–H
alkylation
of
quinoxalin-2(1H)-ones
feedstock
aldehydes,
amides,
alcohols,
ethers,
or
cycloalkanes.
This
reaction
occurred
under
environmentally
benign
and
external
oxidant-free
conditions,
providing
general
sustainable
access
various
C3-alkylated
quinoxalinone
derivatives
broad
substituent
diversity
good
functional
group
compatibility.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(47), С. 9255 - 9271
Опубликована: Янв. 1, 2022
This
Review
provides
the
community
with
a
comprehensive
summary
of
application
Ni-catalyzed
carboboration
strategy
by
carefully
classifying
reaction
types
and
detailing
useful
examples.
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(33)
Опубликована: Апрель 8, 2024
Alkylation
reactions
are
pivotal
in
organic
chemistry,
with
wide-ranging
utilization
across
various
fields
of
applied
synthetic
chemistry.
However,
conventional
reagents
employed
alkylations
often
pose
substantial
health
and
exposure
risks.
Quaternary
ammonium
salts
(QAS)
present
a
promising
alternative
for
these
transformations
offering
significantly
reduced
hazards
as
they
non-cancerogenic,
non-mutagenic,
non-flammable,
non-corrosive.
Despite
their
potential,
use
direct
remains
relatively
unexplored.
This
review
outlines
strategies
utilizing
QAS
alkylation
reactions,
providing
researchers
safer
approaches
to
chemical
synthesis.
