Organic Letters,
Год журнала:
2020,
Номер
22(18), С. 7152 - 7157
Опубликована: Авг. 28, 2020
The
redox-neutral
Ir(III)-
or
Ru(II)-catalyzed
C–H
couplings
of
azomethine
imines
with
α,α-difluoromethylene
alkynes
have
been
realized,
leading
to
the
efficient
synthesis
indenopyrazole
frameworks
via
a
tandem
functionalization/[3
+
2]
dipolar
cycloaddition/ring-opening
aromatization
rearrangement
process,
in
which
generated
fluoroallene
species
was
involved
as
dipolarophile
selective
β-F
elimination
process.
Subsequent
biological
evaluation
revealed
that
these
synthesized
indenopyrazoles
could
serve
interesting
cytotoxic
agents
for
further
development.
Organic Letters,
Год журнала:
2020,
Номер
22(11), С. 4078 - 4082
Опубликована: Май 13, 2020
The
generation
of
2,3-dihydro-benzo[c][1,2]diazepine
derivatives
via
rhodium(III)-catalyzed
[4+3]
annulation
pyrazolidinones
and
propargylic
acetates
is
disclosed.
reaction
proceeds
smoothly
under
relatively
mild
conditions
from
as
novel
C3
synthons.
A
range
dinitrogen-fused
heterocyclic
compounds
are
readily
accessed
by
this
approach.
Advanced Synthesis & Catalysis,
Год журнала:
2020,
Номер
362(22), С. 4861 - 4875
Опубликована: Сен. 21, 2020
Abstract
Benzazepines
and
benzodiazepines,
benzofused
seven‐membered
N‐heterocycles,
compose
an
important
family
of
natural
products
pharmaceuticals.
Although
certainly
effectives,
classical
synthetic
methods
these
cyclic
compounds
involve
methodologies
that
often
require
multistep
procedures,
with
generation
waste
materials
lack
sustainability.
By
contrast,
cycloadditions
based
on
transition
metal
catalyzed
C−H
bond
activations
(oxidative
annulations)
have
emerged
as
appealing
strategies
for
more
sustainable
processes.
In
this
review,
we
focus
our
attention
to
describe
the
state‐of‐the‐art
transition‐metal‐catalyzed
annulations
via
benzazepines
benzodiazepines.
magnified
image
Chemistry - An Asian Journal,
Год журнала:
2019,
Номер
14(24), С. 4520 - 4533
Опубликована: Сен. 18, 2019
Abstract
Strained
ring
systems
are
regarded
as
privileged
coupling
partners
in
directed
C−H
bond
functionalization
and
have
emerged
a
potential
research
area
organic
synthesis.
The
inherent
strain
these
acts
driving
force,
allowing
the
facile
construction
of
diversified
structural
scaffolds
via
integrating
activation
ring‐scission.
mechanistic
underpinnings
allows
implementation
plethora
bonds
across
plentiful
substrates,
including
less
reactive
alkyl
ones.
Considering
synthetic
space,
this
will
foster
developments
novel
methods
chelation
guided
functionalization.
This
review
focus
on
recent
transition‐metal
catalyzed
assisted
concomitant
scission
strained
rings
to
attain
molecular
complexity.
Journal of the American Chemical Society,
Год журнала:
2021,
Номер
143(12), С. 4543 - 4549
Опубликована: Март 17, 2021
We
report
here
a
C–H
homoallylation
reaction
of
aromatic
ketones
with
methylenecyclopropanes
(MCPs)
only
using
catalytic
amount
Fe(PMe3)4.
A
variety
and
MCPs
are
applicable
to
the
form
ortho-homoallylated
selectively
via
regioselective
scission
three-membered
rings.
The
homoallylated
products
amenable
further
elaborations,
providing
functionalized
1,2-dihydronaphthalenes.
Angewandte Chemie International Edition,
Год журнала:
2021,
Номер
60(39), С. 21327 - 21333
Опубликована: Июнь 28, 2021
A
catalytic
system-controlled
divergent
reaction
strategy
was
here
reported
to
construct
four
types
of
intriguing
spiroheterocyclic
skeletons
from
simple
and
readily
available
starting
materials
via
a
precise
chemical
bond
activation/[n+1]
annulation
cascade.
The
tetraazaspiroheterocyclic
trizazspiroheterocyclic
scaffolds
could
be
independently
constructed
by
selective
N-N
cascade,
C(sp2
)-H
activation/[4+1]
novel
tandem
)-H/C(sp3
strategy,
along
with
broad
scope
substrates,
moderate
excellent
yields
valuable
transformations.
More
importantly,
in
these
transformations,
we
are
the
first
time
capture
activation
C(sp3
pyrazolidinones
under
different
system.
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
61(24)
Опубликована: Март 26, 2022
Abstract
Despite
the
widespread
existence
of
chiral
1,4‐diamines
in
bioactive
molecules
and
their
applications
asymmetric
catalysis,
catalytic
synthesis
such
structures
from
readily
accessible
substrates
remains
a
long‐standing
challenge.
Here,
we
report
Cu‐catalyzed
cascade
hydroamination
protocol
to
construct
wide
range
1,4‐diamine
derivatives
high
yields
with
excellent
enatioselectivities
(up
95
%
yield
up
>99
ee).
The
use
two
hydroxylamine
esters
containing
different
functionalized
amino
groups
allowed
us
increase
complexity
final
structures.
desired
products
could
be
easily
transformed
into
NH
2
‐Terfenadine.
Mechanistic
study
demonstrates
that
this
reaction
proceeds
through
ring‐opening
sequence.
Organic Letters,
Год журнала:
2023,
Номер
25(15), С. 2582 - 2587
Опубликована: Апрель 10, 2023
Transition
metal-controlled
divergent
annulation
reactions
of
azomethine
imines
with
iodonium
ylides
via
C-centered
[1,2]-rearrangement
have
been
developed.
The
imino
group,
as
a
switchable
and
transient
directing
group
(DG),
underwent
intramolecular
nucleophilic
addition
in
situ
generated
bicyclic
diaziridine,
which
facilitated
the
subsequent
annulations
presence
different
metal
complexes
catalysts.
benzo[c]chromen-1-one
pyrano[de]isochromene
scaffolds
could
be
independently
constructed
Rh(III)
Ru(II),
respectively.
It
was
worth
noting
that
employed
first
DG
through
rearrangement
progress.
Organic Letters,
Год журнала:
2019,
Номер
21(6), С. 1789 - 1793
Опубликована: Фев. 22, 2019
Chemodivergent
annulative
couplings
have
been
realized
between
N-methoxy
benzamides
and
1,3-enynes
via
Rh-catalyzed
C-H
activation
1,4-Rh
migration.
Under
Rh/copper
catalyzed
aerobic
conditions,
the
nitrogen
annulation
occurred
as
major
pathway.
The
chemoselectivity
was
switched
to
oxygen
under
proper
condition
control
with
stoichiometric
amounts
of
Cu(II)
oxidant
NaOAc.
Both
coupling
systems
proceeded
a
broad
scope
functional
group
tolerance.
Advanced Synthesis & Catalysis,
Год журнала:
2019,
Номер
361(12), С. 2897 - 2903
Опубликована: Март 27, 2019
Abstract
Herein,
we
report
a
Rh(III)‐catalyzed
1,3‐dienylation
of
isoquinolin‐1(2
H
)‐ones
through
C−H
activation.
The
present
reaction
enables
the
preparation
3‐(buta‐1,3‐dien‐2‐yl)isoquinolin‐1(2
direct
cross‐coupling
readily
available
with
methylenecyclopropanes,
while
tolerating
many
sensitive
functional
groups.
Therefore,
this
method
provides
an
efficient
and
convenient
approach
for
modification
interesting
molecules.
magnified
image
