Radical reactions enabled by polyfluoroaryl fragments: photocatalysis and beyond
Chemical Society Reviews,
Год журнала:
2024,
Номер
53(9), С. 4741 - 4785
Опубликована: Янв. 1, 2024
The
review
summarizes
advances
in
the
radical
chemistry
of
polyfluorinated
arenes
under
photocatalytic
conditions.
fluoroaryl
fragment
serves
as
enabling
motif
for
reaction
design
and
efficient
generation
reactive
intermediates.
Язык: Английский
Synthesis of substituted 5,6,7,8‐tetrafluoro‐1H‐benzo[f]indol‐4,9‐diones based on the reaction of hexafluoro‐1,4‐napthoquinone with methyl 3‐aminocrotonates
Journal of Heterocyclic Chemistry,
Год журнала:
2024,
Номер
61(10), С. 1554 - 1563
Опубликована: Июль 23, 2024
Abstract
For
the
first
time,
possibility
of
using
hexafluoro‐1,4‐naphthoquinone
for
construction
condensed
heterocyclic
system
was
demonstrated.
As
a
result,
two‐step
synthesis
previously
unknown
5,6,7,8‐tetrafluoro‐1
H
‐benzo[
f
]indol‐4,9‐dione
derivatives
elaborated.
The
suggested
method
includes
initial
interaction
with
various
methyl
3‐aminocrotonates
and
subsequent
intramolecular
cyclization
into
target
fluorinated
benzo[
]indole‐4,9‐diones.
distinctive
feature
considered
protocol
is
regiospecific
reaction
fluorine
atoms
in
quinone
fragment.
Advantages
presented
approach
are
simple
synthetic
procedure
avoiding
chromatographic
purification,
atom
economy
readily
available
starting
materials.
structure
one
synthesized
compounds
established
by
x‐ray
analysis.
Язык: Английский
Investigation of the reaction of hexafluoro-1,4-naphthoquinone with substituted phenols
Journal of Fluorine Chemistry,
Год журнала:
2025,
Номер
282, С. 110402 - 110402
Опубликована: Фев. 1, 2025
Язык: Английский
Unlocking the Reactivity of the C-In Bond: Alkyl Indium Reagents as a Source of Radicals Under Photocatalytic Conditions
Chemical Science,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
Generation
of
organic
radicals
from
organometallic
compounds
is
a
key
step
in
metallaphotoredox
cross-coupling
reactions.
The
ability
organoindium
to
serve
as
sources
alkyl
under
light
promoted
oxidative
conditions
described.
Organoindium
reagents
were
used
dual
photocatalytic/nickel
with
aryl
bromides.
These
can
be
conveniently
obtained
primary,
secondary
and
tertiary
bromides
chlorides
using
novel
indium(i)
bromide/lithium
bromide
system.
Both
steps,
the
formation
organoindiums
their
are
insensitive
towards
air
moisture
tolerate
wide
variety
functional
groups.
Язык: Английский
Photoinduced radical alkylation of aldehydes with potassium alkyltrifluoroborates
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(14), С. 3988 - 3996
Опубликована: Янв. 1, 2024
A
method
for
radical
addition
at
aldehydes
is
described.
The
reaction
based
on
the
interplay
of
attack
and
cleavage
processes
occurring
a
boron
complexed
carbonyl
group.
Язык: Английский
The Study of Reaction of Hexafluoro‐1,4‐Napthoquinone With Substituted 5‐Aminopyrazoles
Journal of Heterocyclic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 30, 2024
ABSTRACT
For
the
first
time,
interaction
of
perfluoro‐1,4‐naphthoquinone
with
various
5‐aminopyrazoles
was
investigated.
It
shown
that
three
types
products
can
be
obtained
depending
on
structure
starting
aminopyrazole.
all
examples,
substitution
one
fluorine
atom
in
quinone
moiety
observed.
Wherein,
most
cases,
aminopyrazoles
act
as
a
C‐nucleophile
leading
to
2‐(5‐aminopyrazol‐4‐yl)‐3,5,6,7,8‐pentafluoronaphthalene‐1,4‐diones.
At
same
time
substrates
unsubstituted
at
ring
nitrogen
regiospecifically
react
aminogroup
resulting
formation
2,5,6,7,8‐pentafluoro‐3‐((pyrazol‐5‐yl)amino)naphthalene‐1,4‐diones.
Besides
that,
absence
steric
hindrance
pyrazole
unit
allowed
us
direct
process
Position
2
and
synthesize
zwitter‐ionic
3‐(5‐aminopyrazol‐2‐ium‐2‐yl)‐5,6,7,8‐tetrafluoro‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐olates.
The
structures
two
were
confirmed
by
x‐ray
analysis.
Язык: Английский
Current trends in organic chemistry: contribution of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
Russian Chemical Bulletin,
Год журнала:
2024,
Номер
73(9), С. 2423 - 2532
Опубликована: Сен. 1, 2024
Язык: Английский
Synthesis of Substituted N'‐(3,5,6,7,8‐Pentafluoro‐1,4‐Dioxo‐1,4‐Dihydronaphthalen‐2‐yl)Hydrazides by Condensation of Acyl Hydrazines and Perfluoro‐1,4‐Naphthoquinone
ChemistrySelect,
Год журнала:
2024,
Номер
9(43)
Опубликована: Ноя. 1, 2024
Abstract
The
reaction
of
different
acyl
hydrazines
with
hexafluoro‐1,4‐napthoquinone
was
studied
for
the
first
time.
It
demonstrated
that
this
interaction
stops
at
substitution
one
fluorine
atom
in
quinone
moiety.
Based
on
observed
reaction,
a
general
approach
to
synthesis
pentafluoro‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl
hydrazides
developed.
revealed
optimal
conditions
condensation
are
reflux
MeOH
0.25
h;
note,
protocol
does
not
require
any
chromatographic
purification
target
products.
method
is
versatile
and
makes
it
possible
prepare
products
containing
various
substituents
aryl
part
molecule.
In
addition,
alkyl
heteroaryl
can
be
employed
as
starting
compounds
too,
presence
hydroxy
cyano
groups
applied
interfere
condensation.
structure
obtained
products,
namely
4‐chloro‐N□‐(3,5,6,7,8‐pentafluoro‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)benzohydrazide,
confirmed
by
X‐ray
diffraction.
crystals
hydrazide,
both
NH
form
intermolecular
hydrogen
bonds
give
rise
layers
lying
[001]
plane.
Prepared
N'‐(3,5,6,7,8‐pentafluoro‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)hydrazides
interest
redox‐active
ligands
precursors
obtaining
wide
range
functionalized
1,4‐napthoquinones
medicine
chemistry.
Язык: Английский
Electrochemical Oxidation Enables Radical Dearomative Spiroannulation to 2H‐Spiro[benzofuran‐3,9'‐fluoren]‐2‐one
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(43)
Опубликована: Май 25, 2024
Developing
pragmatic
strategies
for
accessing
functional
benzofuran-2-ones
from
3-([1,1'-biphenyl]-2-yl)benzofuran
remains
an
enduring
challenge.
Herein,
we
have
achieved
a
highly
discriminating
electrochemical
oxidative
dearomative
spiroannulation
of
3-([1,1'-biphenyl]-2-yl)benzofuran,
culminating
in
the
synthesis
2H-spiro[benzofuran-3,9'-fluoren]-2-one
derivatives.
By
harnessing
electrophilic
intermediates
benzofuryl
radical
cations
supported
by
DFT
calculations,
attain
exceptional
regioselectivity
while
eliminating
need
stoichiometric
oxidants.
Mechanistic
investigations
reveal
sequence
events
involving
benzofuran
cation,
encompassing
capture
H
Язык: Английский
Photoredox Activation of Fluorinated Organozinc Reagents: Hydrofluoroalkylation of Unactivated and Electron Deficient Alkenes
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(16), С. 11826 - 11835
Опубликована: Июль 26, 2024
Hydrofluoroalkylation
of
alkenes
with
organozinc
reagents
under
photocatalytic
conditions
is
described.
The
fluorinated
alkyl
radicals
were
generated
from
organozincs
by
the
single
electron
oxidation
carbon-zinc
bond.
radical
addition
step
followed
either
hydrogen
atom
transfer
for
unactivated
olefins
or
a
reduction/protonation
sequence
strongly
accepting
arylidenemalononitriles.
Язык: Английский