European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(42)
Опубликована: Сен. 5, 2023
Abstract
Metal‐free,
visible
light‐induced
difunctionalizations
of
α
‐CF
3
styrenes
with
aryl
diazonium
salts
and
various
hetero
nucleophiles
(ROH,
H
2
O,
N
−
F
)
are
described.
This
concise
protocol
provided
easy
access
to
the
tertiary
alkyl
ethers,
alcohol
fluorides
good
yields
excellent
functional
group
tolerance.
In
addition,
four‐component
“SO
”
insertion
reaction
also
worked
efficiently
produce
,
β
‐sulfonyl
ethers
in
moderate
yields.
A
radical‐polar
crossover
coupling
pathway
was
proposed
for
C−O
bond
formation.
Organic Letters,
Год журнала:
2023,
Номер
25(18), С. 3314 - 3318
Опубликована: Май 1, 2023
We
disclose
herein
an
efficient
photochemical
formal
[3+2+1]
annulation
strategy
for
the
transformation
of
diazocarbonyl
compounds
into
various
fluorinated
nitrogen-containing
heterocycles.
This
is
characterized
by
reacting
fluoroalkyl
radicals
with
α-diazoketones,
which
are
used
as
infrequent
denitrogenated
synthons
under
visible
light.
Moreover,
a
wide
range
N-heterocycles
containing
precious
CF3
and
perfluoroalkylated
groups
constructed
in
moderate
to
good
yields.
Notably,
this
may
provide
fruitful
path
synthesis
complex
organofluorides
via
diazo/fluorine/radical
chemistry.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(11), С. 7188 - 7198
Опубликована: Май 12, 2023
Rongalite
has
been
used
as
a
cheap
and
efficient
carbon
synthon
for
the
synthesis
of
divergent
N-heteroaromatics,
including
different
pyridines
quinolines.
The
selective
products
can
be
achieved
by
employing
enaminones
or
enaminones/anilines
reaction
partners.
In
addition,
compared
with
using
conventional
aldehyde
synthons,
rongalite
displays
an
evident
advantage
in
providing
considerably
higher
product
yields
under
milder
conditions.
GC-MS
analysis
process
performed
to
probe
possible
mechanism.
Nature Communications,
Год журнала:
2024,
Номер
15(1)
Опубликована: Июнь 18, 2024
Abstract
Controlling
regioselectivity
during
difunctionalization
of
alkenes
remains
a
significant
challenge,
particularly
when
the
installation
both
functional
groups
involves
radical
processes.
In
this
aspect,
methodologies
to
install
trifluoromethane
(−CF
3
)
via
have
been
explored,
due
importance
moiety
in
pharmaceutical
sectors;
however,
these
existing
reports
are
limited,
most
which
affording
only
corresponding
β-trifluoromethylated
products.
The
main
reason
for
limitation
arises
from
fact
that
−CF
group
served
as
an
initiator
those
reactions
and
predominantly
preferred
be
installed
at
terminal
(β)
position
alkene.
On
contrary,
functionalization
internal
(α)
would
provide
valuable
products,
but
meticulous
approach
is
necessary
win
switch.
Intrigued
by
we
here
develop
efficient
regioselective
strategy
where
α-position
Molecular
complexity
achieved
simultaneous
insertion
sulfonyl
fragment
(−SO
2
R)
β-position.
A
precisely
regulated
sequence
generation
using
red
light-mediated
photocatalysis
facilitates
switch
position.
Furthermore,
demonstrates
broad
substrate
scope
industrial
potential
synthesis
pharmaceuticals
under
mild
reaction
conditions.
Chinese Journal of Chemistry,
Год журнала:
2023,
Номер
41(23), С. 3388 - 3400
Опубликована: Июнь 24, 2023
Comprehensive
Summary
This
review
provides
a
comprehensive
summary
of
progress
to
date
in
the
utilization
rongalite
as
versatile
reagent
organic
synthesis,
with
focus
on
recent
researches.
The
contents
have
been
organized
according
functions
exhibited
by
rongalite.
Reaction
mechanisms
are
provided,
demonstrating
multifaceted
roles
this
compound
various
transformations,
including
sulfone,
C1
or
masked
proton
source
and
single
electron
donor
reducing
agent.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(12), С. 1360 - 1366
Опубликована: Фев. 23, 2024
Comprehensive
Summary
The
conversion
of
CF
3
‐alkenes
to
gem
‐difluoroalkenes
using
reductive
cross‐coupling
strategy
has
received
much
attention
in
recent
years,
however,
the
use
green
and
readily
available
reducing
salt
mediate
these
reactions
remains
be
explored.
In
this
work,
a
concise
construction
gem‐
difluoroalkenes,
which
requires
neither
catalyst
nor
metal
agent,
was
established.
Rongalite,
safe
inexpensive
industrial
product,
employed
as
both
radical
initiator
reductant.
This
procedure
compatible
with
linear
cyclic
diaryliodonium
salts,
enabling
wide
variety
substrates
(>70
examples).
utility
approach
demonstrated
through
gram‐scale
synthesis
efficient
late‐stage
functionalizations
anti‐inflammatory
drugs.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(15), С. 4214 - 4218
Опубликована: Янв. 1, 2024
A
[3
+
1
1]
cascade
annulation
reaction
for
the
divergent
construction
of
trisubstituted
indolizines
using
sulfoxonium
ylides,
BrCF
2
CO
Me
and
pyridinium
salts
as
readily
available
substrates
has
been
developed.
Organic Letters,
Год журнала:
2023,
Номер
25(39), С. 7220 - 7224
Опубликована: Сен. 28, 2023
Herein,
we
disclose
a
straightforward
approach
to
access
transition-metal-free
reductive
N-formylation
of
nitroarenes.
This
reaction
integrates
the
dual
role
rongalite,
which
acts
as
reductant
and
C1
building
block
concurrently.
provides
an
alternative
method
for
synthesis
N-aryl
formamides
from
nitroarenes,
including
construction
C–N
bond.
The
utility
this
protocol
was
demonstrated
by
scale-up
late-stage
functionalizations
complex
molecules.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(8), С. 1727 - 1732
Опубликована: Янв. 1, 2024
In
this
study,
we
developed
a
novel
methodology
involving
base-controlled,
rongalite-mediated
reductive/aldol
reaction,
followed
by
cyclization
of
isatylidene
malononitriles/cyanoacetates,
resulting
in
the
synthesis
spiro[2,3-dihydrofuran-3,3'-oxindole].
Additionally,
have
disclosed
dimerization
process
for
malononitriles,
yielding
dispiro[cyclopent-3'-ene]bisoxindole.
The
utilization
rongalite
reaction
serves
dual
purpose,
acting
both
as
reducing
agent
and
C1
synthon.
approach
has
several
advantages
like
simple
setup,
wide
substrate
scope,
requiring
less
time,
using
water
green
solvent,
no
metal
or
catalyst
is
required
products
can
be
easily
isolated
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(18), С. 5144 - 5150
Опубликована: Янв. 1, 2024
A
transition-metal-free
multi-functionalization
reaction
of
β-trifluoromethyl
enones
and
azacycles
is
first
developed
for
the
synthesis
valuable
amino-2,3-dihydrofuran
derivatives.
Organic Letters,
Год журнала:
2023,
Номер
25(34), С. 6368 - 6373
Опубликована: Авг. 18, 2023
A
chemo-,
regio-,
and
stereoselective
reaction
of
trifluoromethyl
enones,
phenylsilane,
phosphine
oxides
through
a
sequential
hydrodefluorination
defluorophosphorylation
relay
is
developed
for
the
synthesis
distinctive
gem-fluorophosphine
alkenes.
This
multicomponent
occurred
under
transition-metal-free
conditions
with
good
functional
group
tolerance.
Moreover,
preinstalled
carbonyl
auxiliary
important
tuning
reactivity
β-trifluoromethyl
thereby
enabling
controllable
selective
functionalization
two
fluorine
atoms
in
trifluoromethylated
enones.
