Abstract
(Trifluoromethyl)sulfanyl
compounds
have
garnered
significant
attention
in
medicinal
chemistry,
agrochemistry,
and
materials
science
due
to
their
unique
physicochemical
properties,
including
high
lipophilicity,
metabolic
stability,
strong
electron-withdrawing
ability.
This
review
pro-vides
a
comprehensive
overview
of
the
current
methods
for
synthesis
(trifluoromethyl)sulfanyl
compounds,
highlighting
recent
advances
emerging
strategies.
Key
synthetic
approaches,
such
as
direct
(trifluoromethyl)sulfanylation,
transition-metal-catalyzed
processes,
radical-based
are
discussed
with
an
emphasis
on
substrates
reagents.
The
chapter
also
briefly
introduces
mechanistic
insights
role
novel
reagents
enhancing
efficiency
selectivity
these
transformations.
ACS Catalysis,
Год журнала:
2024,
Номер
14(9), С. 6451 - 6461
Опубликована: Апрель 12, 2024
Given
the
abundance
of
alcohol
feedstocks
and
significance
disulfides,
we
herein
report
a
nickel-catalyzed
direct
deoxygenative
disulfuration
alcohols
with
trisulfide
dioxides
to
access
wide
range
disulfide
molecules
without
cumbersome
decoration
coupling
partners.
The
use
readily
available
dicyclohexylcarbodiimide
form
transient
isoureas
provides
activation
high
bond
dissociation
energy
C–O
bond,
which
facilitates
straightforward
conversion
nonderivatized
forge
C–SS
bond.
Notably,
this
method
obviates
preactivation
multistep
procedure
catalytic
turnover
under
exogenous
ligand
base-free
conditions,
featuring
broad
substrate
scope
functional
group
compatibility.
It
thus
offers
robust
alternative
existing
methods
for
precise
construction
versatile
compounds
from
more
abundant
commercially
substrates.
synthetic
utility
was
further
showcased
by
successful
gram-scale
experiments
structurally
complex
pharmaceuticals.
Chemical Reviews,
Год журнала:
2024,
Номер
124(13), С. 8130 - 8232
Опубликована: Июнь 28, 2024
Within
the
canonical
repertoire
of
amino
acid
involved
in
protein
biogenesis,
proline
plays
a
unique
role
as
an
presenting
modified
backbone
rather
than
side-chain.
Chemical
structures
that
mimic
but
introduce
changes
into
its
specific
molecular
features
are
defined
analogues.
This
review
article
summarizes
existing
chemical,
physicochemical,
and
biochemical
knowledge
about
this
peculiar
family
structures.
We
group
analogues
from
following
compounds:
substituted
prolines,
unsaturated
fused
structures,
ring
size
homologues,
heterocyclic,
e.g.,
pseudoproline,
bridged
proline-resembling
overview
(1)
occurrence
nature
their
chemical
synthesis,
(2)
physicochemical
properties
including
conformation
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(24)
Опубликована: Март 13, 2024
Abstract
A
synthetic
method
for
preparation
of
optically
active
trifluoromethylthio
(SCF
3
)
compounds
by
a
copper‐catalyzed
regio‐
and
enantioselective
hydroboration
1‐trifluoromethylthioalkenes
with
H‐Bpin
has
been
developed.
The
hydrocupration
an
in
situ
generated
CuH
species
subsequent
boration
reaction
generate
chiral
SCF
‐containing
alkylboronate,
which
Bpin
moiety
can
be
further
transformed
to
deliver
various
molecules.
Computational
studies
suggest
that
the
group
successfully
controls
regioselectivity
reaction.
Green Chemistry,
Год журнала:
2024,
Номер
26(10), С. 5914 - 5920
Опубликована: Янв. 1, 2024
We
reported
a
direct
simple
trifluoromethylthiolation
reaction
of
various
terminal
alkynes
using
new
hypervalent
trifluoromethylthio-iodine(
iii
)
reagent
TFTI
in
fluorinated
alcohol,
either
hexafluoro-2-propanol
or
perfluoro-
tert
-butanol.
Organic Letters,
Год журнала:
2024,
Номер
26(19), С. 4158 - 4162
Опубликована: Май 2, 2024
Herein,
we
present
a
novel
strategy
for
synthesizing
polyfluorinated
compounds
by
the
fluorotrifluoromethylation
of
olefins,
which
was
achieved
through
new
trifluoromethyl-iodine(III)
reagent
TFNI-1.
TFNI-1
readily
synthesized
via
three-step
process,
and
its
structure
characterized
NMR
spectroscopy
X-ray
crystallography.
It
is
shown
radical
trapping
clock
experiments
that
reaction
involves
CF3
intermediate.
Angewandte Chemie,
Год журнала:
2024,
Номер
136(24)
Опубликована: Март 13, 2024
Abstract
A
synthetic
method
for
preparation
of
optically
active
trifluoromethylthio
(SCF
3
)
compounds
by
a
copper‐catalyzed
regio‐
and
enantioselective
hydroboration
1‐trifluoromethylthioalkenes
with
H‐Bpin
has
been
developed.
The
hydrocupration
an
in
situ
generated
CuH
species
subsequent
boration
reaction
generate
chiral
SCF
‐containing
alkylboronate,
which
Bpin
moiety
can
be
further
transformed
to
deliver
various
molecules.
Computational
studies
suggest
that
the
group
successfully
controls
regioselectivity
reaction.
