Chemical Synthesis,
Journal Year:
2023,
Volume and Issue:
3(4)
Published: July 19, 2023
The
construction
of
d
3
-methylated
all-carbon
quaternary
stereocenters
has
been
successfully
developed
via
carbene-catalyzed
desymmetrization
prochiral
oxindolyl
1,3-diketones.
Three
new
stereogenic
centers
were
efficiently
constructed
with
satisfactory
outcomes.
Diverse
spiro-polycyclic
molecules
a
stereocenter
generated
in
good
to
excellent
yields
diastereoselectivities
and
enantioselectivities.
This
reaction
features
broad
substrate
scope,
functional-group
tolerance,
easy
scale-up.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(7), P. 2112 - 2133
Published: Jan. 1, 2024
Organofluorine
compounds
are
of
high
value.
NHC-catalyzed
fluorination
and
fluoroalkylation
have
served
as
powerful
versatile
vehicles
for
accessing
the
related
organofluorines.
This
review
focuses
on
recent
developments
in
this
area.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(36), P. 5395 - 5398
Published: Jan. 1, 2023
The
first
N-heterocyclic
carbene
organocatalytic
three-component
radical
relay
trifunctionalization
of
unactivated
alkenes
through
the
combination
remote
1,4-cyano
migration
and
alkylacylation
was
reported.
This
protocol
features
mild
reaction
conditions,
readily
available
materials,
excellent
regioselectivity,
capability
late-stage
functionalization.
The Chemical Record,
Journal Year:
2023,
Volume and Issue:
23(7)
Published: March 21, 2023
Abstract
N
‐Heterocyclic
carbene
(NHC)
organocatalysis
has
emerged
as
a
powerful
tool
in
the
field
of
modern
organic
synthesis
especially
asymmetric
construction
various
cyclic
skeletons.
As
an
emerging
NHC‐bound
1,3‐bielectrophilic
intermediate,
alkynyl
acylazolium
drawn
substantial
attention
recent
years,
and
been
used
versatile
3C‐synthon
synthesizing
valuable
molecules
since
its
discovery.
In
this
review,
focused
on
different
pathways
for
formation
acylazoliums
from
precursors
like
alkynoic
esters,
acids
ynals,
advances
transformations
applications
pioneered
or
developed
over
last
decade
under
NHC‐catalysis
were
summarized
comprehensively.
At
same
time,
outlook
further
investigation
exploration
novel
reaction
modes
future
was
also
discussed.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(15), P. 2657 - 2662
Published: April 11, 2023
An
N-heterocyclic
carbene
(NHC)-catalyzed
facile
assembly
of
α-sulfonyl
ketones
has
been
successfully
developed
through
a
radical-mediated
sulfonyl
methylation
readily
available
aldehydes.
This
protocol
involves
the
effective
single-electron
transfer
reduction
α-iodosulfones
by
NHC-bound
Breslow
intermediates,
thus
allowing
subsequent
radical-radical
coupling
to
afford
target
compounds.
Moreover,
catalytic
system
was
found
be
equally
for
difunctionalization
styrenes
and
1,3-enynes
via
three-component
radical
relay
process.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(48)
Published: Oct. 11, 2023
Abstract
N
‐Heterocyclic
carbene
(NHC)
catalyzed
radical‐radical
reactions
have
been
proven
to
be
powerful
strategies
for
assembling
ketyl‐containing
compounds
via
single
electron
transfer
(SET)
pathway
under
either
thermal
conditions
or
photoredox
conditions.
In
this
context,
acylation
of
alkenes
radical
relay
NHC‐organocatalysis
has
also
opened
a
new
window
the
difunctionalization
construct
valuable
molecules
in
organic
synthesis.
review,
advances
and
progress
were
summarized
according
different
ways
generation
key
NHC‐bound
ketyl‐type
radicals.
Furthermore,
reaction
scopes,
limitations
mechanisms
discussed
based
on
types
catalytic
systems.
Conclusions
perspectives
put
forward
at
end.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(38), P. 7047 - 7051
Published: Sept. 19, 2022
Commercially
available
CF2Br2
has
been
used
as
a
convenient
source
for
the
rapid
and
reliable
incorporation
of
gem-difluorovinyl
motif
into
an
allene
framework
via
N-heterocyclic
carbene
catalyzed
difluoroolefination
1,3-enynes.
The
reaction
proceeds
through
cascade
three-component
radical
relay/elimination
process.
This
protocol
is
distinguished
by
its
mild
conditions,
readily
accessible
starting
materials,
wide
substrate
scope,
ease
late-stage
functionalization,
thus
unlocking
untraditional
strategy
to
construct
new
class
functionalized
allenes.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(18), P. 12935 - 12948
Published: Sept. 6, 2023
An
electrochemical
or
photoelectrochemical
regioselective
polyfluoroalkylation/cyclization
cascade
of
3-aza-1,5-dienes
with
sodium
fluoroalkanesulfinates
is
presented.
This
protocol
proceeds
a
broad
substrate
scope
and
good
functional
group
tolerance
under
mild,
oxidant-free,
transition-metal-free,
electrolyte-free
conditions
to
provide
3-polyfluoroalkylated
4-pyrrolin-2-ones
in
one
step
from
readily
available
N-vinylacrylamides,
it
scalable
the
Gram
scale.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(11), P. 2695 - 2700
Published: Jan. 1, 2023
Herein,
a
practical,
convenient
and
facile
construction
of
highly
functionalized
2-pyrrolidinone
enabled
by
N-Heterocyclic
Carbene
(NHC)-catalyzed
radical
tandem
cyclization
has
been
developed.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(7), P. 1669 - 1674
Published: Jan. 1, 2023
N
-Heterocyclic
carbene-catalyzed
difluorocyclopropanation
of
alkenes
with
aldehydes
and
CF
2
Br
for
a
facile
efficacious
synthesis
new
class
functionalized
gem
-difluorocyclopropanes
bearing
acyl
groups
was
developed.
