Journal of Sulfur Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown, P. 1 - 12
Published: Dec. 24, 2024
A
series
of
bis(4-fluorophenylmethylsulfanyldiketones)
were
synthesized
by
multicomponent
thiomethylation
reaction
between
2,4-pentanedione,
α,ω-alkanedithiols,
and
4-fluorobenzaldehyde
in
the
presence
an
organocatalyst.
It
was
found
that
developed
α-monosubstituted
β-diketones
mainly
exist
keto
form.
Considering
green
chemistry
metrics,
prospects
for
industrial
implementation
synthesis
target
molecules
evaluated.
Among
prepared
bis-sulfanyl
diketones,
highest
fungicidal
activity
against
plant
pathogenic
fungi
Bipolaris
sorokiniana,
Fusarium
oxysporum,
Rhizoctonia
solani
compound
containing
a
4,4′-thiodibenzene
spacer
sulfur
atoms
bis(4-fluorophenylmethylsulfanyldiketone)
molecule.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(13), P. 2255 - 2263
Published: May 31, 2023
Abstract
A
catalyst‐
and
oxidant‐free,
highly
efficient,
scalable,
sustainable
synthetic
method
is
developed
for
the
selenylative
annulation
of
2‐alkynyl
biaryls
or
2‐heteroaryl‐substituted
alkynyl
benzenes
with
readily
available
diselenides
under
electrochemical
conditions
to
synthesize
a
wide
variety
selanyl
polycyclic
aromatic
hydrocarbons
heteroaromatics
in
high
excellent
yield
up
99%
at
room
temperature
short
time
(2‐5
h).
The
transformation
required
only
electricity
as
green
reagent
produces
hydrogen
gas
innocuous
byproduct.
Notably,
chemistry
metrics
protocol
are
found
excellent.
Mechanistic
studies
revealed
radical
pathway
being
initiated
by
situ
generation
corresponding
selenyl
from
conditions.
Significantly,
direct
comparison
approach
that
our
previously
iodine‐catalyzed
chemical
not
but
also
more
energy‐efficient,
high‐yielding,
sustainable,
practical.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(55), P. 7057 - 7060
Published: Jan. 1, 2024
A
metal-
and
oxidant-free,
electricity-driven
C–H
selenylative
tellurylative
annulation
of
N
-(2-alkynyl)anilines
with
diorganyl
dichalcogenides
is
developed
to
access
3-chalcogenylquinolines.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(13), P. 1794 - 1797
Published: Jan. 1, 2024
Highly
regio-
and
diastereoselective
synthesis
of
2-thiorganyl
1-bromo
or
1-iodo-1,3-dienes
is
reported
via
1,2-sulfur
migration
propargylic
sulfides.
These
dienes
are
precursors
thiophenes
selenophenes
by
reaction
with
sulfur
selenium.
Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
29(67)
Published: Sept. 12, 2023
In
the
vibrant
field
of
SF5
chemistry,
X
reagents
(X=F,
Cl,
Br)
are
at
heart
current
investigations
in
radical
pentafluorosulfanylation
reactions.
I
is
missing
link
whose
existence
has
not
been
reported
despite
its
potential
as
donor.
This
study
reports
formal
addition
hitherto
unknown
reagent
to
alkynes
by
means
a
combination
Cl/KI/18-crown-6
ether.
The
exclusive
regio-
and
stereoselective
synthesis
unprecedented
(E)-1-iodo-2-(pentafluoro-λ6
-sulfanyl)
alkenes
was
achieved.
A
consensus
reached
through
computational
mechanistic
studies
for
realistic
formation
SF5-
anion
but
solution
rational
involvement
SF5⋅
iodine
radicals
iodo
reaction.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
11(1), P. 171 - 175
Published: Nov. 23, 2023
A
facile
and
metal-free
hydrophosphorodithiolation
of
alkynes
with
P
4
S
10
alcohols
leading
to
vinyl
phosphorodithioates
has
been
developed
under
mild
conditions.
Herein,
we
report
an
HFIP-mediated,
versatile,
sustainable,
atom-economical,
and
regio-
stereoselective
hydro-functionalization
of
ynamides
with
various
S-nucleophiles
(1
equiv.)
such
as
thiols,
thiocarboxylic
acids,
carbamates,
xanthates,
O,O-diethyl
S-hydrogen
phosphorothioate
to
access
a
wide
variety
stereodefined
trisubstituted
ketene
N,S-acetals
under
mild
conditions.
This
protocol
requires
only
HFIP,
which
plays
multiple
roles,
acting
Brønsted
acid
protonate
the
ynamide
regioselectively
at
beta
carbon
generate
reactive
keteniminium
intermediate,
stabilizing
intermediate
solvent
through
H-bonding.
After
nucleophilic
attack
S-nucleophile
on
deprotonation,
HFIP
is
regenerated
in
most
cases
can
be
easily
recovered
recycled,
revealing
high
sustainability
protocol.
Remarkably,
all
reactions
are
highly
efficient
furnish
excellent
yields
many
pure
products
were
obtained
just
by
washing
crude
reaction
mixture
pentane.
Significantly,
green
chemistry
metrics
found
excellent.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(40), P. 8136 - 8140
Published: Jan. 1, 2023
The
widespread
presence
of
bicyclo[1.1.1]pentane
(BCP)
and
sulfur
motifs
in
pharmaceutical
compounds
underscores
the
significance
synthesizing
suitably
functionalized
BCP
thioethers.
In
response,
we
have
developed
a
metal-free
photocatalyst-free
strategy
that
harnesses
visible
light-induced
radical
cascades.
This
approach
culminates
synthesis
essential
thio-BCP
derivatives,
which
serve
as
crucial
precursors
for
formation
corresponding
sulfoxides,
sulfones,
sulfoximines.
Importantly,
this
methodology
exhibits
potential
large-scale
applications,
displaying
commendable
tolerance
towards
various
functional
groups
while
operating
under
mild
reaction
conditions.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(32), P. 6443 - 6484
Published: Jan. 1, 2024
Alkynes
are
important
in
organic
synthesis.
This
review
mainly
focuses
on
the
recent
advances
(2013–2023)
alkynes
with
C–S
bond
formation,
based
more
than
30
kinds
of
sulfur
reagents.
