The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 20, 2024
A
convenient
electrochemical
oxidative
cascade
cyclization
of
alkenes
equipped
with
pendant
alcohols
general
nucleophiles
was
developed.
Using
readily
available
diarylmethanimine
and
carboxylic
acids
as
nucleophilic
sources,
a
broad
range
internal
alkene
terminal
substrates
could
produce
RCO2-
Ar2CN-functionalized
O-heterocycles
in
moderate
to
high
yields
without
the
requirement
for
external
oxidants
metals.
These
resulting
products
can
subsequently
be
hydrolyzed
yield
valuable
NH2-
OH-functionalized
tetrahydrofurans
tetrahydropyranes
under
mild
conditions.
Importantly,
efficient
conversion
secondary
alcohol
amines
complete
inversion
configuration
enhances
methodology,
enabling
construction
2-aryl-3-amino
tetrahydrofuran
complementary
diastereoselectivity.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
11(2), P. 597 - 630
Published: Nov. 23, 2023
This
review
highlights
the
recent
progress
in
electrochemical
difunctionalization
of
alkenes
and
alkynes
involving
C–S/Se
bond
formation
to
access
organochalcogen
frameworks.
Current Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
28(2), P. 105 - 116
Published: Jan. 1, 2024
Abstract:
Sodium
sulfinates
have
been
widely
utilized
as
sulfonyl
radical
precursors
for
preparing
a
diverse
array
of
value-added
sulfur-containing
compounds
(sulfones,
sulfonamides,
sulfonates,
thiosulfonates,
etc.)
through
S-C,
S-N,
S-O
and
S-S
bonds
formation
reactions.
Organic
electrosynthesis
has
become
an
attractive
alternative
to
conventional
methods
redox
reactions
because
it
utilizes
electric
current
instead
chemical
agents.
As
such,
the
electrochemical
generation
radicals
from
sodium
their
applications
in
organic
attracted
much
attention.
In
this
review,
recent
advances
sulfonylation
involving
since
2015
were
reviewed,
along
with
related
reaction
mechanisms.
A
novel
electrochemical
cyclization
reaction
of
N
-acryloyl-indole-3-carboxamides
has
been
developed,
which
provides
a
new
and
efficient
strategy
for
the
synthesis
γ-carbolinone
derivatives.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(20), P. 8273 - 8279
Published: Jan. 1, 2023
An
electrochemical
method
has
been
developed
for
the
synthesis
of
γ-keto
sulfones
with
a
β-quaternary
carbon
center
through
1,2-C
migration
mediated
by
sulfonyl
under
metal-
and
oxidant-free
conditions.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(12), P. 8896 - 8905
Published: June 10, 2024
Endocyclic
1-azaallyl
anions
engage
allyl
acetates
in
a
palladium-catalyzed
allylation
followed
by
reduction
to
give
unprotected
2-(hetero)aryl-3-allylpiperidines
and
2-allyl-3-arylmorpholines,
products
not
easily
accessible
other
means.
The
group
is
then
readily
transformed
into
variety
of
functional
groups.
Preliminary
studies
on
the
asymmetric
variant
reaction
using
an
enantiomerically
pure
BI-DIME-type
ligand
provide
product
with
moderate
enantioselectivity.
Computational
suggest
that
energy
barriers
inner-sphere
reductive
elimination
outer-sphere
nucleophilic
substitution
are
almost
same,
which
makes
both
them
possible
pathways.
In
addition,
mechanism
displays
enantiodiscriminating
C–C
bond
forming
step,
while
much
less
selective,
combined
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
11(1), P. 74 - 82
Published: Nov. 17, 2023
In
the
present
paper,
an
efficient
photoredox-catalyzed
intramolecular
oxy-
and
aminoacylation
of
internal
alkenes
equipped
with
pendant
oxygen-
or
nitrogen-centered
nucleophiles
acyl
oxime
esters
is
reported.
Under
visible-light
irradiation,
a
variety
structurally
diverse
acylated
saturated
heterocycles,
such
as
tetrahydrofurans,
tetrahydropyrans,
δ-valerolactones,
tetrahydropyrroles,
piperidines,
tetrahydro-1,3-oxazepines,
etc.,
were
efficiently
synthesized
from
easily
accessible
unsaturated
alcohols,
carboxylic
acids,
tosyl-protected
amines,
O-homoallyl
benzimidates
via
radical-mediated
cascade
acylation/cyclization
process.
This
light-driven
transformation
features
broad
substrate
scope,
good
functional
group
compatibility,
high
regio-
diastereoselectivity,
mild
reaction
conditions,
representing
general
practical
procedure
toward
construction
heterocycles
well
their
derivatives.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(21), P. 8510 - 8515
Published: Jan. 1, 2023
A
versatile
and
straightforward
electrochemical
system
for
the
synthesis
of
allyl
sulfones
using
readily
accessible
sulfinates
trifluoroborate
salts
is
presented.
Practical
visible-light-induced
synthesis
of
alkyl
sulfones
has
been
achieved
via
a
multicomponent
reaction
aryldiazo
tetrafluoroborate
salts,
styrene
derivatives,
thiophenol
and
sodium
metabisulfite
in
the
presence
rhodamine
B.
