Molecules,
Год журнала:
2023,
Номер
28(14), С. 5615 - 5615
Опубликована: Июль 24, 2023
A
catalyst-free
aza-Michael
addition/C(sp3)-O
bond
formation
tandem
reaction
of
substituted
amino
ferrocenes
with
quinone
esters
was
developed,
which
provided
a
green
and
efficient
strategy
for
the
construction
C(sp3)-O
from
C(sp3)-H,
series
N-ferrocene-substituted
benzodihydrooxazoles
were
smoothly
produced
in
moderate
to
excellent
yields
(up
>99%
yield).
The
mechanism
experiments
showed
that
performed
as
both
substrate
oxidant.
salient
features
this
transformation
include
good
functional
group
tolerance,
broad
scope
mild
conditions.
Precision Chemistry,
Год журнала:
2024,
Номер
2(5), С. 208 - 220
Опубликована: Апрель 23, 2024
The
catalytic
asymmetric
diastereodivergent
synthesis
of
axially
chiral
2-alkenylindoles
was
established
via
phosphoric
acid-catalyzed
addition
reactions
C3-unsubstituted
with
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(24), С. 16567 - 16580
Опубликована: Июнь 7, 2024
Axially
chiral
biaryls
featuring
a
C–N
axis
are
important
functional
molecules
in
diverse
fields.
The
asymmetric
Buchwald–Hartwig
reaction
represents
powerful
strategy
for
these
targets.
Previous
studies,
however,
have
been
predominantly
restricted
to
intramolecular
atroposelective
coupling,
likely
due
the
steric
and
entropic
effects
reductive
elimination
of
Pd(II)
species
with
sterically
congested
aryl
nitrogen
groups.
We
now
report
two
intermolecular
coupling
systems
bulky
NH
lactams
halohydrocarbons
enabled
by
rerouting
mechanism
one
that
accommodates
challenging
substrates.
Both
exhibited
group
tolerance,
excellent
enantioselectivity,
high
Z
selectivity
(if
applicable),
affording
atropisomeric
biaryl
olefins
through
de
novo
construction
axis.
Experimental
computational
studies
were
performed
elucidate
mechanism,
switch
pathways
is
traced
effect
(ortho
substituent)
halide
substrate.
A
2,6-disubstituted
reorients
proximal
lactamide
ligand
its
unusual
O-ligation
mode.
With
amide
oxygen
participation,
this
intermediate
undergoes
an
accessible
barrier
five-membered
ring
transition
state,
pathway
as
well
induction
mode
has
much
underexplored
catalysis.
Abstract
The
efficient
synthesis
of
chiral
2,2‐disubstituted
indolin‐3‐ones
is
great
importance
due
to
its
significant
synthetic
and
biological
applications.
However,
catalytic
enantioselective
methods
for
de
novo
such
heterocycles
remain
scarce.
Herein,
a
novel
cyclizative
rearrangement
readily
available
anilines
vicinal
diketones
the
one‐step
construction
enantioenriched
presented.
reaction
proceeds
through
self‐sorted
[3+2]
heteroannulation/regioselective
dehydration/1,2‐ester
shift
process.
Only
phosphoric
acid
employed
promote
entire
sequence
simplify
manipulation
this
protocol.
Various
common
aniline
derivatives
are
successfully
applied
asymmetric
as
1,3‐binuclephiles
first
time.
Remarkably,
observed
stereoselectivity
proposed
originate
from
an
amine‐directed
regio‐
ortho
‐Csp
2
‐H
addition
ketones.
A
range
transformations
resulting
products
demonstrated
well.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(8), С. 1670 - 1706
Опубликована: Фев. 29, 2024
Abstract
The
Friedel‐Crafts
reaction
stands
as
a
powerful
synthetic
tool
for
C−H
functionalization
of
aromatic
feedstocks,
which
is
conventionally
realized
through
electrophilic
alkylation
and
acylation.
burgeoning
interests
in
axially
chiral
compounds
across
diverse
fields
have
spurred
extensive
exploration
this
classic
transformation
catalytic
atroposelective
synthesis.
Consequently,
the
past
decade
has
witnessed
rapid
expansion
various
non‐canonical
reactions,
including
arylation,
alkenylation,
halogenation,
sulfenylation,
amination
aryl
bonds,
thereby
delving
into
new
chemical
spaces.
A
range
methods
been
devised
these
significant
arene
functionalization.
This
review
provides
comprehensive
overview
cutting‐edge
synthesis
atropoisomers
categorized
three
parts
based
on
type
bond
formation
aromatics:
C(
sp
2
)−C(
3
)
formations,
formations
)−heteroatom
formations.
richness
electrophiles
modulation
atroposelectivity
by
organocatalysts,
particularly
Brønsted
acids,
are
elucidated.
We
anticipate
that
repertoire
asymmetric
will
continue
to
flourish
be
demonstrated
not
only
scientific
researches
but
also
industrial
organic
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(14), С. 3894 - 3899
Опубликована: Янв. 1, 2024
The
first
organocatalyzed
asymmetric
reductive
amination
towards
axially
chiral
N
-arylindoles
proceeding
through
n
→
π*
interaction-induced
dynamic
kinetic
resolution
is
reported.
Chemistry - A European Journal,
Год журнала:
2023,
Номер
30(8)
Опубликована: Ноя. 30, 2023
Carbazole
is
a
heterocyclic
motif
that
can
be
found
in
diverse
array
of
natural
and
unnatural
products
displaying
wide
range
biological
physiological
properties.
Furthermore,
this
heterocycle
part
electronic
materials
like
photoconducting
polymers
organic
optoelectronic
owing
to
its
excellent
photophysical
characteristics.
Consequently,
the
development
synthetic
strategies
for
carbazole
scaffolds
holds
potential
significance
material
fields.
In
regard,
variety
preparation
methods
has
been
developed
exploit
their
efficient
distinct
formation
new
C-C
C-heteroatom
bonds
under
mild
conditions
enabling
broad
substrate
diversity
functional
group
tolerance.
Therefore,
review
focuses
on
synthesis
set
derivatives
describing
methodologies
involve
direct
irradiation,
photosensitization,
photoredox,
electrochemical
thermal
cyclization
reactions.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
11(2), С. 401 - 406
Опубликована: Ноя. 23, 2023
A
facile
access
to
N-fused/helical/spiro-carbazole
scaffolds
through
sequential
annulation
of
bidentate
diamines
with
cyclic
diaryliodonium
salts
has
been
disclosed.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(42)
Опубликована: Сен. 7, 2023
Abstract
A
new
synthetic
approach
to
novel
axially
chiral
iodobenzocarbazole
derivatives
based
on
the
highly
enantioselective
intramolecular
iodoarylation
of
linked
alkyne‐indole
systems
was
developed
by
using
versatile
catalyst,
stereogenic‐at‐cobalt(III)‐complex,
through
an
iodinated
vinylidene
o
‐quinone
methide
(IVQM)
intermediate.
This
protocol
provides
21
examples
in
excellent
yields
with
good
high
enantioselectivities
(up
96
%
yield,
98
ee).
Furthermore,
introduced
iodine
atoms
can
easily
be
converted
into
other
functional
groups.
