Chemical Communications,
Год журнала:
2024,
Номер
60(74), С. 10156 - 10159
Опубликована: Янв. 1, 2024
An
efficient
chalcogenative
annulation
strategy
for
constructing
functionalized
saturated
N-heterocycles
from
unactivated
alkenes
with
dichalcogenides
under
electrochemical
conditions
has
been
presented.
This
protocol
is
applicable
to
mono-,
di-
or
tri-substituted
alkenes,
providing
a
straightforward
pathway
aziridines,
azetidines,
pyrrolidines,
and
piperidines
high
regioselectivity.
Moreover,
the
qualified
realize
oxychalcogenation
of
as
well.
ACS Catalysis,
Год журнала:
2023,
Номер
13(20), С. 13301 - 13309
Опубликована: Окт. 2, 2023
The
construction
of
phosphorus
stereocenters
under
metal-free
conditions
remains
a
formidable
challenge.
Herein,
we
report
mechanistically
distinct
chiral
electrophilic
selenium
catalysis-enabled
desymmetrizing
cyclization
to
access
valuable
phosphorus-stereogenic
heterocycles
with
high
efficiency.
This
ambient
temperature
method
affords
broad
range
compounds
that
bear
phenolic
hydroxyl
group
as
useful
synthetic
handle
and,
thus,
enriches
the
toolbox
for
rapid
generation
molecular
complexity.
control
experiments
and
DFT
calculations
indicate
dual-hydrogen-bonding
bridge
formed
between
substrate
TfO–
anion
plays
crucial
role
in
determining
enantioselectivity
transformation.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(10), С. 7029 - 7038
Опубликована: Март 1, 2024
Enantioselective
difunctionalization
of
alkenes
offers
a
straightforward
means
for
the
rapid
construction
enantioenriched
complex
molecules.
Despite
tremendous
efforts
devoted
to
this
field,
enantioselective
aminative
remains
challenge,
particularly
through
an
electrophilic
addition
fashion.
Herein,
we
report
unprecedented
approach
via
copper-catalyzed
with
external
azo
compounds
as
nitrogen
sources.
A
series
valuable
cyclic
hydrazine
derivatives
either
[3
+
2]
cycloaddition
or
intramolecular
cyclization
have
been
achieved
in
high
chemo-,
regio-,
enantio-,
and
diastereoselectivities.
In
transformation,
wide
range
functional
groups,
such
carboxylic
acid,
hydroxy,
amide,
sulfonamide,
aryl
could
serve
nucleophiles.
Importantly,
new
cyano
oxazoline
chiral
ligand
was
found
play
crucial
role
control
enantioselectivity.
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(21)
Опубликована: Янв. 11, 2024
Abstract
The
discovery
and
synthetic
applications
of
novel
organoselenium
compounds
their
reactions
proceeded
rapidly
during
the
past
fifty
years
such
processes
are
now
carried
out
routinely
in
many
laboratories.
At
same
time,
growing
demand
for
new
enantioselective
provided
challenges.
convergence
selenium
chemistry
asymmetric
synthesis
led
to
key
developments
1970s,
although
majority
early
work
was
based
on
stoichiometric
processes.
More
recently,
greater
emphasis
has
been
placed
greener
catalytic
variations,
along
with
a
deeper
understanding
mechanisms.
present
review
covers
literature
this
field
from
2010
2023
encompasses
mediated
by
chiral
selenium‐based
reagents,
auxiliaries,
especially,
catalysts.
Protocols
achiral
conjunction
other
species
catalysts,
as
well
that
controlled
substrates,
also
included.
Nature Communications,
Год журнала:
2025,
Номер
16(1)
Опубликована: Март 3, 2025
A
highly
enantioselective
electrophilic
selenylation/semipinacol
rearrangement
of
allenols
has
been
developed,
which
is
enabled
by
the
cooperative
catalysis
a
chiral
sulfide
and
an
achiral
sulfonic
acid.
The
designed
synthesized
catalyst
selenylating
reagent
play
crucial
role
in
enhancing
both
enantioselectivity
reactivity.
This
approach
exhibits
excellent
regio-,
chemo-,
enantioselectivity,
providing
access
to
diverse
enantioenriched
cyclopentanones
featuring
arylselenovinyl-substituted
quaternary
carbon
stereocenter.
Furthermore,
these
products
can
be
transformed
into
synthetically
valuable
alkyne,
vinyl
bromide,
aniline
derivatives.
Mechanistic
studies
reveal
that
combination
acid
not
only
facilitates
formation
catalytically
active
species,
but
also
governs
reaction.
Meanwhile,
density
functional
theory
calculations
disclose
four
hydrogen
bond
interactions
π‧‧‧π
interaction
are
responsible
for
observed
enantioselectivity.
Rearrangement
reactions
serve
as
steps
syntheses
biologically
provide
intellectual
conceptual
curiosities
within
broad
field
organic
chemistry.
Here,
authors
report
allenols,
catalysed
Lewis
base.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(5), С. 3054 - 3067
Опубликована: Фев. 16, 2023
A
three-component
oxychalcogenation
reaction,
from
alkenes,
diselenides/thiophenols,
and
H2O/alcohols,
has
been
realized
herein.
Tetrabutylammonium
tribromide
(TBATB)
dimethylsulfoxide
(DMSO)
are
utilized
as
the
catalyst
terminal
oxidant,
respectively,
to
enable
this
difunctionalization
transformation.
The
metal-free
reaction
system
shows
good
functional
group
compatibility,
providing
a
unified
practical
approach
access
β-hydroxyl
or
β-alkoxy
organochalcogenides.
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(23), С. 3974 - 4005
Опубликована: Окт. 20, 2022
Abstract
Halogen
(fluorine,
chlorine,
bromine,
iodine)
or
chalcogen
(sulfur,
selenium)‐containing
heterocycles
are
widely
recognized
as
key
building
blocks
in
many
natural
products
and
bioactive
targets.
Catalytic
asymmetric
halogenation/chalcogenation
of
carbon‐carbon
unsaturated
bonds
via
onium
ion
transformations
efficient
methods
to
obtain
diverse
chiral
heterocyclic
backbones.
In
the
past
few
years,
catalytic
enantioselective
versions
halo/thio/seleno‐functionalizations
with
various
halogen
electrophiles
have
experienced
constant
development.
This
review
highlights
those
advances
preparing
functionalized
promoted
by
organocatalysts
metal‐based
catalysts.
magnified
image
ACS Omega,
Год журнала:
2022,
Номер
7(44), С. 39531 - 39561
Опубликована: Окт. 27, 2022
Sulfonyl
hydrazides
are
viewed
as
alternatives
to
sulfinic
acids
and
their
salts
or
sulfonyl
halides,
which
broadly
used
in
organic
synthesis
work
active
pharmaceutical
substances.
Generally,
considered
good
building
blocks
show
powerful
value
a
diverse
range
of
reactions
construct
C–S
bonds
C–C
bonds,
even
C–N
sulfur,
carbon,
nitrogen
sources,
respectively.
As
profound
synthetic
tool,
the
electrosynthesis
method
was
recently
achieve
efficient
green
applications
hydrazides.
Interestingly,
many
unique
novel
electrochemical
syntheses
using
radical
precursors
have
been
developed,
including
cascade
reactions,
functionalization
heterocycles,
well
continuous
flow
combining
with
since
2017.
Accordingly,
it
is
necessary
specifically
summarize
recent
developments
only
more
deeply
understand
better
design
reactions.
Herein,
research
2017
reviewed
detail
based
on
chemical
structures
products
reaction
mechanisms.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(11), С. 7431 - 7447
Опубликована: Май 23, 2023
Three-component
selenofunctionalization
processes
of
olefins,
diselenides
and
sulfonamides,
water,
alcohols,
or
acids
utilizing
1-fluoropyridinium
triflate
(FP-OTf)
as
a
reaction
promoter
are
reported.
Under
the
optimal
conditions,
broad
range
vicinally
functionalized
selenide
derivatives
was
accessible
with
high
yields
excellent
functional
group
compatibilities.
Mechanistic
studies
revealed
that
FP-OTf
played
key
role
in
this
process.
