Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(8)
Опубликована: Янв. 5, 2024
Abstract
Dearomative
spirocyclization
reactions
represent
a
promising
means
to
convert
arenes
into
three‐dimensional
architectures;
however,
controlling
the
regioselectivity
of
radical
dearomatization
with
nonactivated
afford
spirocyclizative
1,2‐difunctionalization
other
than
its
kinetically
preferred
1,4‐difunctionalization
is
exceptionally
challenging.
Here
we
disclose
novel
strategy
for
dearomative
1,2‐
or
1,4‐amidoximation
(hetero)arenes
enabled
by
direct
visible‐light‐induced
homolysis
N−NO
bonds
nitrosamides,
giving
rise
various
highly
regioselective
amidoximated
spirocycles
that
previously
have
been
inaccessible
required
elaborate
synthetic
efforts.
The
mechanism
and
origins
observed
regioselectivities
were
investigated
control
experiments
density
functional
theory
calculations.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(4), С. 2789 - 2797
Опубликована: Янв. 18, 2024
Dearomative
photocycloaddition
of
monocyclic
arenes
is
an
appealing
strategy
for
comprehending
the
concept
"escape
from
flatland".
This
brings
replacement
readily
available
planar
aromatic
hydrocarbon
units
with
a
3D
fused
bicyclic
core
sp3-enriched
carbon
units.
Herein,
we
outline
intermolecular
approach
dearomative
phenols.
In
order
to
circumvent
ground-state
aromaticity
and
construct
conformationally
restrained
building
blocks,
bicyclo[1.1.0]butanes
were
chosen
as
coupling
partners.
renders
straightforward
access
bicyclo[2.1.1]hexane
unit
cyclic
enone
moiety,
which
further
contributed
synthetic
linchpin
postmodifications.
Mechanistic
experiment
advocates
plausible
onset
both
reactants,
depending
on
redox
potential.
Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
8(6), С. 1364 - 1383
Опубликована: Янв. 1, 2021
This
review
summarizes
the
recent
progresses
(2016–2020)
in
hydride
transfer-enabled
C(sp3)–H
activation
according
to
reaction
types,
categorized
into
intramolecular/intermolecular
functionalization,
and
reduction.
Organic Letters,
Год журнала:
2021,
Номер
23(17), С. 6691 - 6696
Опубликована: Авг. 16, 2021
A
novel
and
efficient
strategy
for
trifluoromethylthiolation
dearomatization
of
activated
alkynes
with
stable
readily
available
AgSCF3
has
been
developed.
Reported
herein
is
the
unprecedented
electrochemical
generation
SCF3
radical
in
absence
persulfate
synthesis
SCF3-containing
spiro[5,5]trienones
good
yields
via
a
6-exo-trig
cyclization.
Green Chemistry,
Год журнала:
2022,
Номер
24(13), С. 5058 - 5063
Опубликована: Янв. 1, 2022
The
electrochemical
annulation
of
enaminones/analogous
enamines
and
thioureas
providing
2-aminothiazoles
has
been
realized.
Modulating
the
electrolyte
enables
diastereoselective
synthesis
4,5-dialkoxyl
thiazolines
by
dearomatization.
Journal of Agricultural and Food Chemistry,
Год журнала:
2022,
Номер
70(35), С. 10693 - 10707
Опубликована: Авг. 23, 2022
Spiro
compounds
are
biologically
active
organic
with
unique
structures,
found
in
a
wide
variety
of
natural
products
and
drugs.
They
do
not
readily
lead
to
drug
resistance
due
their
mechanisms
action
have,
therefore,
attracted
considerable
attention
regarding
pesticide
development.
Analyzing
structure-activity
relationships
(SARs)
summarizing
the
characteristics
spiro
high
activity
crucial
steps
design
development
new
pesticides.
This
review
mainly
summarizes
insecticidal,
bactericidal,
fungicidal,
herbicidal,
antiviral,
plant
growth
regulating
functions
provide
insight
for
creation
compound
Chemistry - An Asian Journal,
Год журнала:
2023,
Номер
18(9)
Опубликована: Март 15, 2023
Electrochemical
dearomative
spirocyclization
serves
as
a
green
and
sustainable
approach
to
convert
the
flat,
two-dimension
aromatic
feedstock
into
value-added
three-dimension
spirocyclic
architectures.
This
review
highlights
recent
advances,
emphasizes
mechanistic
discussions,
showcases
synthetic
applications
of
this
emerging
versatile
powerful
transformation.
The Journal of Organic Chemistry,
Год журнала:
2020,
Номер
86(1), С. 917 - 928
Опубликована: Дек. 7, 2020
We
developed
a
green
method
for
the
synthesis
of
spiro[4.5]trienones
through
an
electrochemical
oxidative
halocyclization
with
N-aryl
alkynamides.
This
reaction
was
conducted
under
metal-catalyst-
and
exogenous-oxidant-free
conditions
at
room
temperature.
Using
readily
available
LiCl,
LiBr,
LiI
as
halogen
source,
variety
dearomative
halo-spirocyclization
products
were
obtained
in
good
to
excellent
yields
broad
scope
functional
group
tolerance.
