Green Synthesis and Catalysis,
Год журнала:
2022,
Номер
5(2), С. 131 - 135
Опубликована: Окт. 20, 2022
An
unprecedented
electrochemical
oxidative
trifunctionalization
of
olefins
with
diaryl
disulfides/aryl
thiols
and
N-chlorosuccinimide
in
an
aqueous
system
is
developed.
Two
C–Cl
bonds,
one
C–S
bond,
SO
bond
are
produced
simultaneously
step
from
simple
commercially
available
starting
materials
clean
energy.
This
tandem
methodology
features
as
mild
reaction
conditions,
transition
metal
additional
oxidant
free,
broad
substrate
scope,
good
functional
group
compatibility,
gram
scale
preparation.
ACS Catalysis,
Год журнала:
2021,
Номер
11(12), С. 7513 - 7551
Опубликована: Июнь 9, 2021
Catalytic
functionalization
of
alkynes
with
organoboron
reagents
provides
a
straightforward
access
to
stereochemically
defined
multisubstituted
alkenes,
which
are
structural
motifs
commonly
found
in
bioactive
compounds
and
organic
materials.
Recent
progress
has
substantially
broadened
the
scope
this
field
on
several
fronts.
Strategies
for
regioselectivity
control
1,2-migratory
insertion
across
unsymmetrical
internal
alkynes,
as
well
direct
products
anti-insertion
stereochemistry,
have
been
devised.
The
alkenyl-to-aryl
1,4-metal
migration
upon
metal
recently
exploited
powerful
cascade
sequences
leading
complex
polycyclic
scaffolds,
including
development
enantioselective
processes.
Elegant
enantiospecific
dynamic
kinetic
resolution
methods
developed
accessing
chiral
allenes
from
propargylic
alcohol
derivatives.
Mechanistic
manifolds
emerged
based
single-electron
transfer
(SET)
that
provided
fresh
impetus
alkyne
1,2-difunctionalization
complementary
stereoselectivity
processes
relying
1,2-insertion
R–M
species.
Herein,
we
discuss
most
recent
advances
transition-metal-catalyzed
using
reagents,
categorized
according
type
mechanistic
outcome.
Emphasis
is
placed
aspects,
synthetic
utility,
limitations,
challenges
future
research.
Asian Journal of Organic Chemistry,
Год журнала:
2022,
Номер
11(5)
Опубликована: Март 9, 2022
Abstract
Alkynes
are
one
of
the
most
fundamental
and
diverse
functional
groups
utilized
in
organic
synthesis.
Over
past
few
years,
development
efficient
synthetic
methodologies
for
functionalization
alkynes
has
been
an
active
area
research.
A
plethora
alkyne
reactions
have
reported
literature
to
construct
functionalized
alkene
scaffolds,
which
important
building
blocks
many
natural
products,
pharmaceuticals,
key
intermediates
various
transformations.
In
this
review,
we
describe
recent
advances
with
emphasis
on
substrate
scope,
limitations,
regioselectivity
control
applications
these
reactions.
This
review
covers
from
2016
2021.
Organic Letters,
Год журнала:
2023,
Номер
25(47), С. 8451 - 8456
Опубликована: Ноя. 16, 2023
The
three-component
reactions
of
enaminones,
disulfides,
and
alcohols
for
the
synthesis
polyfunctionalized
alkenes
have
been
realized
via
C-H
C-N
bond
transformation
on
enaminones.
proceed
in
a
novel
"alkene-to-alkene"
difunctionalization
mode
without
using
any
transition
metal.
application
alkene
products
divergent
sulfenyl
heteroaryls,
including
sulfenylated
pyrazoles,
pyrimidines,
isoxazoles,
simple
annulation
has
also
verified.
Journal of the American Chemical Society,
Год журнала:
2021,
Номер
143(10), С. 4074 - 4082
Опубликована: Март 4, 2021
Here
we
report
the
first
example
of
alkyne
trifunctionalization
through
simultaneous
construction
C-C,
C-O,
and
C-N
bonds
via
gold
catalysis.
With
assistance
a
γ-keto
directing
group,
sequential
gold-catalyzed
hydration,
vinyl-gold
nucleophilic
addition,
gold(III)
reductive
elimination
were
achieved
in
one
pot.
Diazonium
salts
identified
as
both
electrophiles
(N
source)
oxidants
(C
source).
Vinyl-gold(III)
intermediates
revealed
effective
nucleophiles
toward
diazonium,
facilitating
addition
with
high
efficiency.
The
rather
comprehensive
reaction
sequence
was
excellent
yields
(up
to
95%)
broad
scope
(>50
examples)
under
mild
conditions
(room
temperature
or
40
°C).
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
61(14)
Опубликована: Янв. 28, 2022
The
structural
diversity
of
sp3
-triorganometallic
reagents
enhances
their
potentiality
in
the
modular
construction
molecular
complexity
chemical
synthesis.
Despite
significant
achievements
on
preparation
1,1,1-
and
1,1,2-triorganometallic
B,B,B-reagents,
catalytic
approaches
that
enable
installation
multiple
boryl
groups
at
skipped
carbons
unactivated
alkenes
still
remain
elusive.
Herein,
we
report
a
cobalt-catalyzed
selective
triborylation
reaction
to
access
synthetically
versatile
1,1,3-triborylalkanes.
This
protocol
provides
general
platform
for
regioselective
trifunctionalization
alkenes,
its
utility
is
highlighted
by
synthesis
various
value-added
chemicals
from
readily
accessible
alkenes.
Mechanistic
studies,
including
deuterium-labelling
experiments
evaluation
potential
reactive
intermediates,
provide
insight
into
experimentally
observed
chemo-
regioselectivity.
Chemical Communications,
Год журнала:
2023,
Номер
59(42), С. 6383 - 6386
Опубликована: Янв. 1, 2023
The
tunable
reactions
of
enaminones
with
phosphine
oxides/phosphonates
in
the
form
vicinal-
and
geminal
diphosphorylation,
C–N
bond
phosphorylation
have
been
developed,
providing
new
methods
for
synthesis
divergent
phosphorylated
molecules.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
unknown
Опубликована: Июнь 25, 2024
We
herein
describe
the
first
example
of
ligand-controlled,
copper-catalyzed
regiodivergent
asymmetric
difunctionalization
terminal
alkynes
through
a
cascade
hydroboration
and
hydroallylation
process.
The
catalytic
system,
consisting
(R)-DTBM-Segphos
CuBr,
could
efficiently
achieve
1,1-difunctionalization
aryl
alkynes,
while
ligand
switching
to
(S,S)-Ph-BPE
result
in
1,2-difunctionalization
exclusively.
In
addition,
alkyl
substituted
especially
industrially
relevant
acetylene
propyne,
were
also
valid
feedstocks
for
1,1-difunctionalization.
This
protocol
is
characterized
by
good
functional
group
tolerance,
broad
scope
substrates
(>150
examples),
mild
reaction
conditions.
showcase
value
this
method
late-stage
functionalization
complicated
bioactive
molecules
simplifying
synthetic
routes
toward
key
intermediacy
natural
product
(bruguierol
A).
Mechanistic
studies
combined
with
DFT
calculations
provide
insight
into
mechanism
origins
ligand-controlled
regio-
stereoselectivity.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
11(1), С. 171 - 175
Опубликована: Ноя. 23, 2023
A
facile
and
metal-free
hydrophosphorodithiolation
of
alkynes
with
P
4
S
10
alcohols
leading
to
vinyl
phosphorodithioates
has
been
developed
under
mild
conditions.
ChemistrySelect,
Год журнала:
2021,
Номер
6(11), С. 2716 - 2744
Опубликована: Март 17, 2021
Abstract
Imidazo[1,2‐
a
]pyridine
is
an
important
nitrogen‐containing
heterocycle
from
biological
as
well
pharmaceutical
point
of
view.
In
recent
years,
regioselective
functionalization
C−H
bond
imidazo[1,2‐
extensively
carried
out
using
various
transition
metal‐based
catalysts.
Alkenylation,
arylation,
dual
dehydrogenative
annulations,
formylation,
thiolation,
aminomethylation,
dicarbonylation,
phosphonylation
along
with
other
significant
reactions
are
the
progress
in
field
imidazopyridine.
Most
these
functionalizations
done
at
C‐3
position
scaffold
and
addition
to
that
development
towards
C‐5
regioselectivity
also
available.
this
review,
our
aim
present
advances
for
employing
metal
catalysts
under
reaction
conditions.
