The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 12, 2024
A
simple
and
high-yielding
strategy
to
produce
a
variety
of
β-keto
sulfides
using
asymmetrical
symmetrical
thiosulfonates
with
ketones
under
mild
conditions
is
reported.
It
was
found
that
the
various
substituted
compounds,
both
electron-withdrawing
electron-donating
substituents,
afforded
wide
range
thiosulfones
(α-thioaryl-β-keto
sulfones)
in
moderate
high
yields.
The
transformations
were
reliable
at
gram-scale,
thus
illustrating
their
efficiency
practicality.
plausible
mechanism
for
protocol
also
proposed.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(7), С. 1450 - 1466
Опубликована: Фев. 14, 2024
Abstract
Due
to
amine
derivatives
widely
existing
in
numerous
clinical
medicines
and
bioactive
compounds,
their
synthesis
has
received
considerable
attention
over
the
past
few
decades.
Traditional
methods
for
of
largely
relied
on
reduction
nitroarenes,
amides,
hydrazines,
nitriles,
azides.
Recently,
discovery
2‐azaallyl
anions
as
super‐electron‐donors
(SEDs)
opened
up
new
possibilities
construction
diverse
carbon‐carbon
carbon‐heteroatom
bonds
through
radical
coupling
strategies.
This
breakthrough
highlights
potential
generating
radicals
versatile
intermediates
organic
synthesis.
Then,
hydrolysis
product
can
easily
separate
corresponding
derivatives.
Thus,
tremendous
been
paid
C−H
functionalization
ketimines
an
alternative
strategy
Herein,
we
comprehensively
summarize
recent
progress
strategies
enabled
by
SEDs.
Their
proposed
mechanistic
pathways,
advantages,
limitations
are
also
discussed
detail.
1.
Introduction
2.
C−C
Bond
Formation
2.1.
Vinylation
Ketimines
2.2.
Arylation
2.3.
Alkylation
2.3.1.
Methylation
2.3.2.
Other
3.
C−X
3.1.
C−P
C−S
Bonds
3.2.
C−N
C−O
4.
Conclusions
Herein
is
reported
a
novel
transition-metal-free
intermolecular
C(sp3)–H/C(sp3)–H
coupling
of
N-tert-butyl
arylamides
with
N-benzyl
imines
through
single-electron
transfer
(SET)
and
1,5-hydrogen
atom
(1,5-HAT)
strategies.
2-Azaallyl
anions
as
super-electron-donors
(SEDs)
undergo
SET
to
generate
2-azaallyl
radicals
amidyl
radicals.
The
radical
undergoes
1,5-HAT
process
form
C-centered
radical,
which
subsequently
coupled
new
C–C
bonds.
This
method
avoids
the
use
transition
metals
photoredox
catalysts
good
functional
group
tolerance
yields
(29
examples,
87%
yield).
Radical
clock
trapping
experiments
provide
significant
evidence
for
A
novel
transition-metal-free
radical
coupling
of
2-azaallyl
anions
for
the
synthesis
α-amino
ketones
has
been
developed.
Easily
accessible
thioesters
and
undergo
single
electron
transfer
(SET)
to
generate
acyl
radicals,
which
participate
in
intermolecular
with
good
functional
group
tolerance
yields
(31
examples,
up
98%
yield).
telescoped
gram-scale
derivatization
product
illustrate
potential
synthetic
utility
this
method.
Radical
trapping
clock
experiments
support
proposed
pathway
between
generated
radical.
Chemical Science,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 3, 2024
Hydrogen
atom
transfer
(HAT)
processes
provide
an
important
strategy
for
selective
C-H
functionalization.
Compared
with
the
popularity
of
1,5-HAT
processes,
however,
net-1,2-HAT
reactions
have
been
reported
less
frequently.
Herein,
we
report
a
unique
visible-light-mediated
amidyl
radicals
synthesis
β-amido
ketone
derivatives.
Single-electron
(SET)
to
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(4), С. 2516 - 2524
Опубликована: Фев. 6, 2024
Using
commercially
available
tertiary
amines
as
an
organic
electron
donor
(OED),
the
reduction
of
"push–pull"
C–C
single
bond
and
reductive
decyanation
tetrahydroisoquinolines
were
realized.
These
reactions
exhibited
higher
reaction
efficiency
better
functional
group
tolerance
compared
with
those
metallic
reductants,
mechanistic
study
indicated
that
a
radical
intermediate
was
involved
in
bond,
which
provides
new
way
to
OED-enabled
mild
reduction.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(23)
Опубликована: Апрель 25, 2024
Abstract
A
mini
review
focused
on
the
chemistry
of
selenosulfones
reported
since
2019
is
here
presented.
Initially,
methods
aimed
to
preparation
such
moiety
are
discussed.
Successively
1,2‐,
1,3‐,
1,4‐
and
1,7‐addition
reactions
C−C
single
multiple
bonds
illustrated.
The
forth
chapter
focuses
electrophilic
aromatic
substitutions.
fifth
deals
with
C−H
functionalizations
while
sixth
one
shows
aryl
diazonium
salts
or
its
precursors.
radical
coupling
redox
active
reagents,
subject
section
seventh.
Selenosulfones
challenged
in
nucleophilic
substitutions
phosphorus‐containing
compounds
shown
eight
nine
followed
by
conclusions
perspectives
section.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Июнь 3, 2024
Comprehensive
Summary
Unsymmetric
sulfides
and
selenides
have
great
applications
in
the
pharmaceutical
field.
Herein,
we
describe
reductive
coupling
reaction
of
xanthate
esters
with
sulfur‐containing
selenium‐containing
compounds
(thio(seleno)sulfonates
disulfides(selenides))
under
nickel‐catalyzed
condition.
It
provides
a
mild
effective
method
for
synthesis
unsymmetric
which
has
advantages
conditions,
high
yields
wide
range
substrates.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 8342 - 8356
Опубликована: Май 31, 2024
A
mild
and
transition-metal-free
defluorinative
alkylation
of
benzyl
amines
with
trifluoromethyl
alkenes
is
reported.
The
features
this
protocol
are
easy-to-obtain
starting
materials,
a
wide
range
substrates,
functional
group
tolerance
as
well
high
atom
economy,
thus
offering
strategy
to
access
variety
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
A
photoinduced
FeCl
3
/HCl
synergistic
catalytic
method
enables
C(sp
)–S
bond
formation
via
reductive
cross-coupling
of
activated/inert
)–H
and
aryl/alkyl
sulfonyl
chlorides
through
ligand-to-metal
charge
transfer
(LMCT).
