The Chemical Record,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 16, 2024
Abstract
Alkylation
reactions
and
their
products
are
considered
crucial
in
various
contexts.
Synthetically,
the
alkylation
of
a
nucleophile
is
usually
promoted
using
hazardous
alkyl
halides.
Here,
we
aim
to
highlight
potential
pnictogen
(ammonium
or
phosphonium)
chalcogen
salts
(sulfonium,
selenonium,
telluronium)
function
as
alkylating
agents.
These
compounds
can
be
non‐volatile
electrophilic
reservoirs.
We
will
center
our
discussion
on
strategies
developed
recent
years
expand
synthetic
utility
these
terms
transferable
groups,
substrate
scope,
product
selectivity.
Herein,
we
present
a
versatile
method
for
synthesizing
unsymmetrical
diarylmethanes
and
diarylketones
from
aldehydes
arenes.
This
involves:
(1)
regioselective
Ar-H
alkylation
to
form
benzhydrylphosphonium
salts
via
one-pot,
four-component
reaction
with
simple
reagents
(2)
chemoselective
reductions
or
oxidations
of
the
benzylic
C-P
bond.
Notably,
D2O
yield
fully
deuterated
diarylmethanes.
high-yielding,
straightforward
approach
offers
valuable
building
blocks
enables
novel
transformations
academic
pharmaceutical
research.
Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
12(5)
Опубликована: Март 23, 2023
Abstract
A
copper‐catalyzed
[3+2]
annulation
of
the
in
situ
generated
pyridinium
ylides
with
α‐CF
3
ketones
was
realized,
which
first
acted
as
synthetic
equivalents
unstable
fluoroalkynones.
With
this
protocol,
a
series
functionalized
2‐fluoroindolizines
were
afforded
moderate
to
good
yields
under
ambient
conditions
air
oxidant.
Organic Letters,
Год журнала:
2024,
Номер
26(7), С. 1447 - 1451
Опубликована: Фев. 14, 2024
Difluoroenoxysilane,
a
commonly
used
difluoroallylating
reagent,
has
attracted
considerable
attention
in
recent
years.
However,
its
application
the
annulation
reaction
for
construction
of
fluorinated
heterocyclic
compounds
remains
relatively
limited.
Presented
here
is
Brønsted
acid-catalyzed
efficient
formal
[4
+
2]
difluoroenoxysilanes
with
α-cyano
chalcones.
The
developed
protocol
demonstrates
tolerance
to
various
substituents
under
mild
conditions,
providing
reliable
approach
construct
gem-difluoro-3,4-dihydro-2H-pyrans
good
excellent
yields
high
diastereoselectivities.
Organic Letters,
Год журнала:
2023,
Номер
25(48), С. 8733 - 8738
Опубликована: Ноя. 22, 2023
A
photoredox-catalyzed
approach
for
the
difluoroalkylation
of
amino
acids
was
achieved
through
simultaneous
decarboxylation
and
defluorination
processes.
This
innovative
protocol
employs
commonly
available
trifluoroacetophenones
as
primary
starting
materials,
eliminating
necessity
preactivation.
strategy
has
enabled
synthesis
several
difluoroketone
functionalized
amines
in
moderate
to
impressive
yields.
These
synthesized
compounds
are
presented
foundational
molecules
subsequent
modification.
The
underlying
mechanism
transformation
is
anchored
a
single
electron
transfer
(SET)
radical
pathway.
Organic Letters,
Год журнала:
2023,
Номер
25(34), С. 6396 - 6400
Опубликована: Авг. 23, 2023
Herein,
we
report
a
straightforward
practical
method
for
efficiently
obtaining
diverse
range
of
thiophosphonium
salts.
This
involves
the
direct
coupling
commercially
available
thiols
and
aldehydes
with
Ph3P
TfOH.
The
setup
is
simple
carried
out
in
metal-free
manner.
synthetic
utility
these
salts
demonstrated
through
various
examples
C-P
bond
functionalizations,
enabling
synthesis
thioether,
deuterated
thioester,
dithioester
derivatives.
These
products,
which
serve
as
valuable
building
blocks,
are
obtained
high
yields.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(28), С. 5724 - 5728
Опубликована: Янв. 1, 2024
Herein,
a
novel
electroreductive
carboxylation
of
benzylphosphine
salts
with
CO
2
through
cleavage
the
C(sp
3
)-P
bond
was
reported
under
conditions
without
redox
reagents
and
noble
metal
catalysts.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(9), С. 1413 - 1418
Опубликована: Апрель 12, 2023
Abstract
Hexafluoroisopropanol
(HFIP)
has
been
extensively
applied
in
organic
synthesis
as
a
versatile
reaction
media.
However,
the
application
of
HFIP
an
catalyst
rarely
studied.
Presented
here,
is
example
HFIP‐catalyzed
Mannich‐type
between
quinoxalin‐2(1
H
)‐ones
and
difluoroenoxysilanes.
The
developed
protocol
tolerates
various
substituents
under
mild
conditions,
providing
divergent
approach
to
construction
difluoro‐substituted
3,4‐dihydroquinoxalin‐2(1
monofluoroquinoxalin‐2(1
51–92%
yields.
magnified
image
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(11), С. 1871 - 1876
Опубликована: Апрель 26, 2023
Abstract
An
aerobic
coupling
of
benzhydryl
phosphonium
salts
with
simple
alkenes
for
accessing
trisubstituted
olefins
is
developed
under
metal‐free,
catalyst‐free,
and
additive‐free
conditions.
New
C(
sp
3
)−C(
2
)
bond
constructed
via
the
C−P
C−H
functionalization
by
synergistically
using
O
as
a
“green”
oxidant
DMSO
promoter.
The
method
also
distinguishes
itself
its
broad
substrate
scope
synthetic
potential.
Particularly,
use
1,3,5‐trimethoxybenzene
fragment
in
resulting
products
carbon‐based
leaving
group
further
transformations
proved
to
be
feasible.
In
this
chapter,
we
have
summarized
some
special
and
representative
transformations
using
DMSO
as
a
green
solvent
in
organic
synthesis
over
the
last
5
years.
contrast
to
previous
reviews,
focus
more
on
situ
activation
pattern
of
by
summarizing
different
fragmentation
processes
show
reaction
initiation
pathway.
For
example,
Pummerer-type,
Selectfluor-enabled,
electrocatalytic-enabled,
photocatalytic-enable
were
classified
discussed
detail.
each
pattern,
several
recent
are
listed,
along
with
their
selected
products
generality,
while
detailed
mechanism
is
also
provided
after
example
facilitate
reader's
understanding
illustrate
chemical
principles.
We
believe
that
chapter
provides
unique
perspective
lead
better
DMSO-mediated
integrated
information
for
researchers
who
keen
select
method
activation.
