Organic Letters,
Год журнала:
2023,
Номер
25(48), С. 8672 - 8676
Опубликована: Ноя. 22, 2023
Direct
thioesterification
of
aldehydes
with
thiols
catalyzed
by
readily
accessible
rare
earth/lithium
amide
RE[N(SiMe3)2]3(μ-Cl)Li(THF)3
is
developed,
which
enables
the
preparation
a
range
thioesters
(31
examples)
under
room
temperature
and
solvent-free
conditions,
without
using
any
additive
or
external
oxidant.
This
method
provides
straightforward
atom-efficient
approach
for
thioester
synthesis.
European Journal of Organic Chemistry,
Год журнала:
2022,
Номер
2022(48)
Опубликована: Дек. 2, 2022
Abstract
Thioester
constitutes
a
fundamentally
unique
intermediate,
engaged
in
various
biosynthesis
processes
living
systems
as
well
versatile
synthon
modern
organic
synthesis.
Transition
metal
catalysis
and
radical
reaction
manifolds
have
enabled
to
enrich
the
repertoire
of
synthetic
methods
for
thioesters.
In
this
review,
we
accommodated
recent
reports
on
strategies
towards
thioester
synthesis
from
plethora
readily
available
feedstocks,
such
alkenes,
alkynes,
alcohols,
phenols
or
commodity
chemicals/synthetic
building
blocks
like
aldehydes,
halides
organoboron
reagents
under
domains.
Furthermore,
momentous
advancements
employing
progenitors
odorous
thiols
CO‐surrogates
contextually
been
emphasized,
alongside
utilization
native
free
CO
gas.
Abstract
Herein,
we
have
accomplished
a
simple
visible
light
mediated
protocol
for
the
cross
dehydrogenative
coupling
of
arylthiols
with
indoles
in
excellent
yields.
Eosin
Y
disodium
salt
is
used
as
photocatalyst
generating
arylsulfur
radical
under
blue
irradiation
confirmed
by
quenching,
scavenging
and
EPR
studies.
Among
synthesized
arylthioindoles,
5‐bromo‐3‐((4‐methoxyphenyl)thio)‐1H‐indole
possess
antibacterial
properties.
These
3‐arylthioindoles
were
further
transformed
into
indolyl‐3‐arylsulfones
indolyl‐3‐arylsulfoxides,
potent
class
non‐nucleoside
reverse
transcriptase
inhibitors
against
human
immunodeficiency
virus
(HIV)
type
I.
Organic Letters,
Год журнала:
2024,
Номер
26(15), С. 3043 - 3047
Опубликована: Апрель 5, 2024
We
disclose
a
deconstructive
[5
+
1]
annulation
protocol
for
the
synthesis
of
isoquinolones
through
nitrogen
insertion
into
abundant
indanones.
This
method
exploits
photoredox-catalyzed
ring-opening
oxime
esters.
The
reaction
proceeds
smoothly
with
water
as
medium
and
tolerates
range
functional
groups
on
diverse
thiophenols,
amines,
or
Moreover,
representative
exhibit
promising
antifungal
activities.
Chemical Communications,
Год журнала:
2024,
Номер
60(52), С. 6671 - 6674
Опубликована: Янв. 1, 2024
The
direct
thioesterification
of
carboxylic
acids
was
catalysed
by
a
pyridine–borane
complex,
and
this
protocol
features
broad
substrate
scope
good
functional
group
tolerance
extends
the
utility
complexes
as
new
catalysts.
ACS Applied Materials & Interfaces,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 24, 2025
Covalent
organic
frameworks
(COFs)
serve
as
an
outstanding
platform
for
heterogeneous
photocatalysis.
We
synthesized
two
analogous
pyrene-based
two-dimensional
COFs
with
π-conjugated
networks,
one
linked
by
C═N
bonds
and
the
other
C═C
bonds,
through
Schiff
base
Knoevenagel
condensation
reactions,
respectively.
investigated
impact
of
these
linkages
on
photocatalytic
activity
COFs,
using
visible-light-mediated
thioesterification
a
model
reaction.
It
was
found
that
olefin-linkage
COF
outperformed
imine-linkage
photocatalyst.
The
developed
protocol
demonstrated
broad
substrate
scope,
including
35
diverse
carboxylic
acids,
14
drug
molecules,
several
disulfide
coupling
partners,
achieving
up
to
95%
yield
thioesters.
practical
utility
this
strategy
is
further
its
successful
application
in
gram-scale
reactions.
photocatalyst
robust
successfully
reused
multiple
cycles
without
any
loss
catalytic
activity.
backbone
facilitated
enhanced
electron
transfer
upon
light
irradiation,
enabling
cross-coupling
acid
reductive
cycle.
Catalysis Science & Technology,
Год журнала:
2022,
Номер
13(2), С. 305 - 309
Опубликована: Дек. 6, 2022
Using
eosin
Y
and
KI
as
photocatalysts
to
facilitate
the
conversion
of
quinoxaline-2(1
H
)-one
phenylhydrazine
hydrochloride
compounds
into
corresponding
3-arylated
)-one,
a
simple
efficient
synthesis
method
has
been
developed.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(23), С. 4233 - 4240
Опубликована: Окт. 27, 2023
Abstract
A
nickel‐catalyzed
reductive
cross
coupling
reaction
of
carboxylic
acids
with
disulfides
is
described.
The
readily
available
and
inexpensive
acid
activated
in
situ
by
the
formation
a
mixed
anhydride.
transformation
occurs
at
room
temperature
wide
functional
group
tolerance
to
efficiently
generate
structurally
diverse
thioesters.
Moreover,
tolerated
broad
substrate
scope,
including
sterically
hindered
disulfides.
Ultimately,
this
powerful
method
could
be
applied
late‐stage
functionalization
for
construction
thioesters,
affording
convenient
practical
tactic
construct
carbon‐sulfur
bonds.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
88(1), С. 640 - 646
Опубликована: Дек. 20, 2022
The
combination
of
visible
light
irradiation
and
Pd-catalysis
has
been
practically
employed
for
the
C-H
alkylation
reactions
naphthylamines
α-diazo
esters,
leading
to
synthesis
α-naphthyl
functionalized
acetates
via
C-C
bond
construction
under
mild
reaction
conditions
solvent-free
conditions.
proven
play
a
pivotal
role
in
reactions,
probably
by
promoting
generation
active
carbene
species
from
esters.
