The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(22), С. 15101 - 15113
Опубликована: Ноя. 9, 2022
Precise
control
of
the
chemoselectivity
halogenation
a
substrate
equipped
with
multiple
nucleophilic
sites
is
highly
demanding
and
challenging.
Most
reported
chlorinations
methyl
ketones
show
poor
compatibility
or
even
exclusive
selectivity
toward
electron-rich
arene,
olefin,
alkyne
residues.
This
attributed
to
direct
in
situ
employment
electrophilic
Cl2/Cl+
species.
Here,
we
that,
bearing
those
competitive
residues,
can
still
undergo
dichlorination
afford
α,α-dichloroketones
chemo-specific
manner.
Enabled
by
I2-dimethyl
sulfoxide
catalytic
system,
which
hydrochloric
acid
only
acts
as
Cl–
donor,
this
straightforward
reaction
safe
operator-friendly
has
high
atomic
economy,
giving
access
structurally
diverse
good
yields
functional-group
tolerance.
Beilstein Journal of Organic Chemistry,
Год журнала:
2025,
Номер
21, С. 564 - 595
Опубликована: Март 13, 2025
Formaldehyde
emerges
as
a
cornerstone
in
multicomponent
reactions,
mainly
prized
for
its
robust
reactivity.
Yet,
alongside
these
beneficial
traits,
this
highly
reactive
C1-building
block
raises
concerns,
primarily
regarding
toxicity.
One
notable
issue
is
the
challenge
of
controlling
formation
undesired
byproducts
during
reactions.
This
review
explores
alternative
blocks
that
serve
surrogates
formaldehyde,
aiming
to
mitigate
some
challenges
associated
with
use
By
identifying
alternatives,
toxicity
concerns
and
improved
reaction
control
can
be
addressed,
paving
way
more
efficient
sustainable
synthetic
methodologies.
Molecules,
Год журнала:
2020,
Номер
25(24), С. 5900 - 5900
Опубликована: Дек. 13, 2020
The
functionalization
of
C–H
bonds
has
become
a
major
thread
research
in
organic
synthesis
that
can
be
assessed
from
different
angles,
for
instance
depending
on
the
type
catalyst
employed
or
overall
transformation
is
carried
out.
This
review
compiles
recent
progress
synthetic
methodology
merges
along
with
cleavage
C–C
bonds,
either
intra-
intermolecular
fashion.
manuscript
organized
two
main
sections
according
to
substrate
which
bond
takes
place,
basically
attending
scission
strained
unstrained
bonds.
Furthermore,
related
works
have
been
grouped
basis
mechanistic
aspects
transformations
are
out,
i.e.,:
(a)
classic
transition
metal
catalysis
where
organometallic
intermediates
involved;
(b)
processes
occurring
via
radical
generated
through
use
initiators
photochemically;
and
(c)
reactions
catalyzed
mediated
by
suitable
Lewis
Brønsted
acid
bases,
molecular
rearrangements
take
place.
Thus,
throughout
wide
range
approaches
show
combination
single
operations
serve
as
platform
achieve
complex
skeletons
straightforward
manner,
among
them
interesting
carbo-
heterocyclic
scaffolds.
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(12), С. 3060 - 3069
Опубликована: Апрель 27, 2021
Abstract
A
metal‐free
approach
for
the
synthesis
of
5‐trifluoromethyl‐1,2,4‐triazoles
via
I
2
‐mediated
[4+1]
annulation
readily
available
trifluoroacetimidohydrazides
and
methyl
ketones
has
been
achieved.
The
transformation
involves
iodination/Kornblum
oxidation,
intermolecular
dehydration
condensation
an
iodine‐mediated
intramolecular
cyclization/aromatization
sequence.
developed
protocol
can
be
easily
scaled
up
to
3
mmol
scale
without
obvious
efficiency
decrease
implemented
by
a
consecutive
one‐pot
manner.
magnified
image
Organic & Biomolecular Chemistry,
Год журнала:
2021,
Номер
19(34), С. 7333 - 7347
Опубликована: Янв. 1, 2021
The
direct
use
structurally
simple
ketones
as
α-ketone
radical
sources
for
α-C(sp3)-H
functionalization
is
a
sustainable
and
powerful
approach
constructing
complex
multifunctional
chemical
scaffolds
with
diverse
applications.
reactions
of
radicals
alkenes,
alkynes,
enynes,
imides,
imidazo[1,2-a]pyridines
have
broadened
the
structural
diversity
complexity
ketones.
Through
chosen
illustrative
examples,
we
outline
recent
progress
in
development
methods
that
enable
ketones,
an
emphasis
on
initiation
systems
possible
mechanisms
transformations.
application
these
strategies
illustrated
by
synthesis
several
biologically
active
molecules
drug
molecules.
Further
subdivision
based
substrate
type
reaction
type.
Asian Journal of Organic Chemistry,
Год журнала:
2021,
Номер
10(7), С. 1795 - 1800
Опубликована: Май 26, 2021
Abstract
A
copper‐catalyzed
oxidative
coupling
strategy
has
been
developed
for
the
synthesis
of
4(3
H
)‐quinazolinones
and
benzoimidazoquinazoline
using
glucose
as
renewable
C
1
synthon.
Isotope
labelling
studies
13
6
D
‐glucose
DMSO‐
d
confirmed
role
source.
The
significant
features
this
method
include
(i)
utilization
0.25
to
0.5
equiv.,
a
multi‐C
synthon;
(ii)
biomass‐derived
platform
chemical
carbon
(iii)
atom‐economical
benign
conditions
and;
(iv)
naturally
occurring
alkaloid
precursor.
Organic Letters,
Год журнала:
2021,
Номер
23(9), С. 3453 - 3459
Опубликована: Апрель 21, 2021
A
visible-light-induced
[3+2]
oxidative
cyclization
of
various
alkynes
with
easily
available
ketene
dithioacetals
as
the
previously
unknown
thiavinyl
1,3-dipoles
in
presence
an
acridine
photosensitizer
is
reported.
series
multisubstituted
thiophenes
were
achieved
regioselectively
≤98%
yields
under
very
mild
metal-free
conditions
without
other
additives.
This
reaction
could
tolerate
a
wide
range
substrates
and
achieve
good
efficiency
large-scale
syntheses.
The
mechanism
their
applications
are
described
detail
to
reveal
reactivity
new
selectivity
reactions.
New Journal of Chemistry,
Год журнала:
2021,
Номер
45(44), С. 20486 - 20518
Опубликована: Янв. 1, 2021
The
preparation
of
heterocyclic
compounds
has
attracted
great
attention
in
organic
chemistry
because
their
extensive
application
the
field
bioactive
molecules,
materials
science,
and
natural
products.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(17), С. 12141 - 12147
Опубликована: Авг. 17, 2021
A
novel
iodine
promoted
cyclization
of
enaminone
with
aryl
methyl
ketones
has
been
developed
as
a
straightforward
method
for
constructing
2-hydroxy-pyrrol-3(2H)-ones.
This
strategy
affords
structurally
diverse
2-hydroxy-pyrrol-3(2H)-ones
rings
in
high
yields.
Moreover,
quarternary
alcohol
constructed
efficiently
the
reaction.
Product
purification
required
only
washing
CH2Cl2
solvent,
thereby
avoiding
traditional
chromatography
and
recrystallization,
making
this
an
example
group-assisted
chemistry.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(3), С. 2917 - 2928
Опубликована: Янв. 13, 2021
An
unprecedented
C(CO)–C(Ar)
bond
cleavage
of
β-enaminones
has
been
realized
under
mild
and
transition-metal-free
conditions.
The
cascade
transformation
based
on
this
C–C
involves
1,3-O/C
migration
aerobic
hydroxylation
leads
to
various
5-hydroxy-1H-pyrrol-2(5H)-ones
with
broad
functional
group
tolerance.
application
methodology
showcased
by
preparing
5-alkoxy-1H-pyrrol-2(5H)-one
derivatives
a
pyrrolo[2,1-a]isoquinolin-3-one
derivative.
