Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 30, 2024
A
visible-light
induced
intermolecular
hydroamination
of
alkenes
with
azoles
is
reported,
delivering
pharmaceutically
valuable
N-benzyl
in
high
yields
excellent
Markovnikov
selectivity.
Mechanistic
studies
suggest
that
the
process
initiated
by
energy
transfer
excited
photocatalyst
alkenes,
followed
single
electron
reduction,
protonation,
and
subsequent
oxidation
to
afford
key
alkyl
carbocation
intermediate.
This
protocol
exhibits
advantages
broad
functional
group
tolerance,
atom
economy,
efficiency,
mild
reaction
conditions.
ChemistrySelect,
Journal Year:
2025,
Volume and Issue:
10(6)
Published: Feb. 1, 2025
Abstract
An
efficient
metal/peroxide‐free
[5
+
1]
cyclization
of
2‐vinylanilines
with
TBN
was
realized
to
access
various
cinnolines
high
yields.
In
addition,
benzo[
e
]pyrrolo[2,1‐c][1,2,4]triazines
could
also
be
obtained
by
using
2‐(1
H
‐pyrrol‐1‐yl)anilines
as
the
raw
materials.
This
cascade
system
selected
common/low‐cost
tert
‐butyl
nitrite
N1
source,
which
performed
broad
substrate
scopes/simple
operation/mild
conditions/available
scaled
up
1
mmol.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 28, 2025
An
effective
trifluoromethyl
radical
addition
to
the
thiocarbonyl
of
thioamide
derivatives
is
described,
which
produces
various
trifluoromethylthiolated
N-heterocycles
such
as
6-(trifluoromethylthio)phenanthridine,
2-(trifluoromethylthio)indole,
and
2-(trifluoromethylthio)benzothiazole
under
visible-light
irradiation.
The
process
features
advantages
mild
reaction
conditions,
a
cheap
easily
available
source
(CF3Br),
green
energy,
well
broad
substrate
scope.
mechanism
investigated
in
detail,
scale-up
experiments
are
performed.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(38)
Published: Aug. 3, 2023
Abstract
Due
to
their
high
lipophilicity
and
strong
electron‐withdrawing
property,
more
attention
has
been
paid
introducing
trifluoromethylseleno
fluoroalkylseleno
moieties
into
organic
molecules.
In
this
short
review,
we
categorize
the
synthesis
of
compounds
that
combine
selenium
fluorinated
two
main
types:
trifluoromethylselenolation
(CF
3
Se)
fluoroalkylselenolation
(R
f
Se,
except
CF
Se).
This
review
aims
provide
a
summary
recent
advances
in
direct
C−H
from
reagents
application.
Based
on
method
how
R
Se
group
was
introduced,
content
is
divided
three
parts:
transition‐metal‐free
reactions,
transition‐metal‐mediated/catalyzed
reactions
photo‐catalyzed
reactions.
The
general
substrate
scope,
mechanism
limitations
would
also
be
discussed
so
hope
will
serve
as
an
inspiration
for
further
research
appealing
field.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(10), P. 2068 - 2072
Published: March 1, 2024
An
efficient
copper-catalyzed
selective
fluoromethylthiolation
of
an
inert
δ-C(sp3)–H
bond
in
sulfonamides
was
reported.
In
the
presence
a
copper
catalyst
and
PhSO2SRf,
radical
generated
through
1,5-hydrogen
atom
transfer
(HAT)
sufficiently
trapped
by
instead
copper,
which
prevalent
metal-catalyzed
radical-relay
processes,
incorporating
fluoromethylthio
group
into
molecules.
The
general
substrate
scope
mild
conditions
endowed
method
with
wide
potential
applications
pharmaceuticals
agrochemicals.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(17)
Published: March 11, 2024
Abstract
Molecules
containing
ether
skeletons
are
widely
present
in
drugs,
natural
products,
functional
materials,
and
life
science.
Direct
C(sp
3
)−H
bond
functionalization
is
considered
a
powerful
strategy
for
the
construction
of
novel
derivatives.
Photo‐/electro‐chemical
technology
relatively
green
sustainable
synthesis
method,
which
opens
up
broad
application
prospect
field
direct
bonds.
In
recent
years,
photo‐/electro‐mediated
alkylation,
arylation,
alkynylation,
esterification,
mercaptoylation,
sulfidation,
amination
ethers
have
been
extensively
studied.
this
review,
research
progress
compounds
from
2014
to
2023
systematically
reviewed,
scope,
limitations,
mechanisms
some
reactions
discussed.
Synthesis,
Journal Year:
2024,
Volume and Issue:
unknown
Published: May 29, 2024
Abstract
The
trifluoromethylthio
(SCF3)
and
trifluoromethylselanyl
(SeCF3)
groups
possess
high
electron-withdrawing
ability,
excellent
lipophilicity,
good
stability,
bioavailability,
they
are
promising
structural
motifs
in
drug
design
development.
Photoredox
catalysis
has
clear
benefits;
it
is
a
mild
sustainable
methodology
for
the
modification
of
chemical
structures
that
enables
variety
reactions
unattainable
using
classical
ionic
chemistry.
This
review
focuses
on
light-initiated
trifluoromethylthiolation
trifluoromethylselenolation
with
diverse
SCF3
SeCF3
reagents.
Representative
transformations
either
photocatalysts
or
through
EDA
complexes,
as
well
possible
reaction
mechanisms,
all
discussed
this
article.
1
Introduction
2
Photocatalyzed
Trifluoromethylthiolation
2.1
MSCF3
(M
=
H,
[Me4N],
Ag)
2.2
XSCF3
(X
Cl,
CF3S)
2.3
ArSO2SCF3
2.4
N–SCF3
Reagents
2.5
Other
3
Trifluoromethylselenolation
3.1
[Me4N][SeCF3]
3.2
ArSO2SeCF3
4
Summary
Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
29(41)
Published: May 8, 2023
Herein,
the
tandem
synthesis
of
various
CF3
Se-containing
heterocyclic
compounds
has
been
developed,
using
Tf2
O
as
catalyst
and
trifluoromethyl
selenoxides
electrophilic
trifluoromethylselenolation
reagents.
This
process
is
characterized
by
its
mild
conditions,
ease
operation,
good
functional
group
compatibility.
A
variety
alkynes
could
be
transferred
into
indoles,
benzofurans,
benzothiophenes,
isoquinolines
chromenes
in
yields.
key
step
involving
formation
Se
species
was
proposed.
ChemCatChem,
Journal Year:
2023,
Volume and Issue:
15(18)
Published: July 5, 2023
Abstract
Carbon‐fluorine
bond
being
highly
polar
in
nature,
its
presence
pharmaceutically
active
molecules
has
huge
impact
on
their
chemical
and
physical
properties.
However,
fluorine
electronegative
small
size,
limits
nucleophilicity
to
the
large
extent;
hence
incorporation
of
organic
is
not
an
easy
task.
Due
this,
demand
for
a
suitable
catalyst
fluorination
reaction
been
raised,
which
lowers
activation
energy
these
reactions
makes
C−F/CF
3
formation
kinetically
more
feasible.
Silver
late
transition
metal
efficiently
used
catalyze
several
chemistry
substantial
potential
reactions.
This
Review
shows
silver
catalyzed
trifluoromethylation
synthesis
F/CF
containing
aromatic,
aliphatic
heterocyclic
compounds.
All
sections
have
elaborated
using
general
discussion
method,
exploration
substrate
scope,
insight
into
mechanistic
studies
shortcomings
methods.
After
reading
this
article
readers
can
develop
detailed
understanding
concept
be
explored
synthesizing
biological
interest.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(19), P. 4905 - 4911
Published: Jan. 1, 2023
Herein,
we
have
reported
a
metal-free
Lewis-acid-catalyzed
divergent
trifluoromethylselenolation
of
alkynes
to
construct
α-trifluoromethylselenolated
ketones
and
trifluoromethylselenolated
alkynes.
