The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(21), С. 14809 - 14818
Опубликована: Окт. 26, 2022
A
one-pot
three-component
synthesis
of
multifunctionalized
isoquinolones
from
2-oxazolines,
iodonium
ylides,
and
carboxylic
acids
via
Rh(III)-catalyzed
oxazolinyl-directed
C-H
activation
tandem
annulation
under
redox-neutral
conditions
has
been
developed.
This
catalytic
system
is
characterized
by
readily
available
starting
materials,
a
wide
tolerance
functional
groups,
short
reaction
time,
high
yields.
The
synthetic
utility
the
cascade
was
further
demonstrated
gram-scale
derivatization
obtained
products.
Chemical Society Reviews,
Год журнала:
2022,
Номер
51(7), С. 2759 - 2852
Опубликована: Янв. 1, 2022
C-H
functionalization
has
been
emerging
as
a
powerful
method
to
establish
carbon-carbon
and
carbon-heteroatom
bonds.
Many
efforts
have
devoted
transition-metal-catalyzed
direct
transformations
of
Metal
carbenes
generated
in
situ
from
transition-metal
compounds
diazo
or
its
equivalents
are
usually
applied
the
transient
reactive
intermediates
furnish
catalytic
cycle
for
new
C-C
C-X
bond
formation.
Using
this
strategy
unactivated
simple
alkanes
complex
molecules
can
be
further
functionalized
transformed
multi-functionalized
compounds.
In
area,
carbene
insertion
bonds
paid
continuous
attention.
Diverse
catalyst
design
strategies,
synthetic
methods,
potential
applications
developed.
This
critical
review
will
summarize
advance
dated
up
July
2021,
by
categories
aliphatic
C(sp3)-H,
aryl
(aromatic)
C(sp2)-H,
heteroaryl
(heteroaromatic)
C(sp2)-H
bonds,
alkenyl
alkynyl
C(sp)-H,
well
asymmetric
more
coverage
given
recent
work.
Due
rapid
development
future
directions
topic
also
discussed.
give
authors
an
overview
chemistry
with
focus
on
systems
Chemical Reviews,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 13, 2024
Hypervalent
iodine(III)
compounds
have
found
wide
application
in
modern
organic
chemistry
as
environmentally
friendly
reagents
and
catalysts.
iodine
are
commonly
used
synthetically
important
halogenations,
oxidations,
aminations,
heterocyclizations,
various
oxidative
functionalizations
of
substrates.
Iodonium
salts
arylating
reagents,
while
iodonium
ylides
imides
excellent
carbene
nitrene
precursors.
Various
derivatives
benziodoxoles,
such
azidobenziodoxoles,
trifluoromethylbenziodoxoles,
alkynylbenziodoxoles,
alkenylbenziodoxoles
group
transfer
the
presence
transition
metal
catalysts,
under
metal-free
conditions,
or
using
photocatalysts
photoirradiation
conditions.
Development
hypervalent
catalytic
systems
discovery
highly
enantioselective
reactions
chiral
represent
a
particularly
recent
achievement
field
chemistry.
Chemical
transformations
promoted
by
many
cases
unique
cannot
be
performed
any
other
common,
non-iodine-based
reagent.
This
review
covers
literature
published
mainly
last
7-8
years,
between
2016
2024.
Organic Letters,
Год журнала:
2023,
Номер
25(24), С. 4422 - 4428
Опубликована: Июнь 8, 2023
Presented
herein
is
a
condition-controlled
selective
synthesis
of
pyranone-tethered
indazoles
or
carbazole
derivatives
via
the
cascade
reactions
N-nitrosoanilines
with
iodonium
ylides.
Mechanistically,
formation
former
involves
an
unprecedented
process
including
nitroso
group-directed
C(sp2)–H
bond
alkylation
N-nitrosoaniline
ylide
followed
by
intramolecular
C-nucleophilic
addition
to
moiety,
solvent-assisted
cyclohexanedione
ring
opening,
and
transesterification/annulation.
On
contrary,
latter
initial
annulation
denitrosation.
These
developed
protocols
feature
easily
controllable
selectivity,
mild
reaction
conditions,
clean
sustainable
oxidant
(air),
valuable
products
that
are
structurally
diverse.
In
addition,
utility
was
showcased
their
facile
diverse
transformations
into
synthetically
biologically
interesting
compounds.
Organic Letters,
Год журнала:
2024,
Номер
26(24), С. 5136 - 5140
Опубликована: Июнь 7, 2024
Herein,
we
report
a
rhodium-catalyzed
C–H
activation/[4+2]
cyclization
reaction
between
α,β-unsaturated
amides
and
iodonium
ylides
for
the
synthesis
of
novel
7,8-dihydroquinoline-2,5-diones
analogues.
This
protocol
provides
series
pyridones
fused
with
saturated
cycles
good
functional
group
compatibility,
water
air
tolerance,
to
excellent
yields
under
mild
green
conditions.
Additionally,
scale-up
can
be
smoothly
performed
as
low
0.25
mol
%
catalyst
loading.
Recycling
experiments
different
transformation
were
also
carried
out
demonstrate
potential
synthetic
utility
this
protocol.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(8), С. 2181 - 2186
Опубликована: Янв. 1, 2022
We
developed
a
catalytic
system-controlled
tunable
strategy
for
the
divergent
synthesis
of
cinnolines
and
pyrazolo[1,2-
]cinnolines
via
rhodium-catalyzed
[4
+
2]
cyclization
easily
available
pyrazolidinones
iodonium
ylides.
Chemical Communications,
Год журнала:
2022,
Номер
58(41), С. 6140 - 6143
Опубликована: Янв. 1, 2022
Highly
selective
and
switchable
[4+2]
annulations
of
2-arylindoles
with
iodonium
ylides
were
achieved
by
performing
solvent-controlled
Rh(III)-catalyzed
C-H
activations.
When
using
DCM
as
a
solvent,
the
functionalization
selectively
delivered
indolo[2,1-a]isoquinoline
derivatives.
In
contrast,
same
catalytic
system
polar
HFIP
solvent
predominately
provided
benzo[a]carbazole
moieties.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(5), С. 1112 - 1116
Опубликована: Янв. 1, 2022
The
direct
synthesis
of
isocoumarin
skeletons
has
been
realized
through
the
Rh(
iii
)-catalyzed
[3
+
3]
annulation
sulfoxonium
ylides
and
iodonium
under
mild
conditions.
Organic Letters,
Год журнала:
2022,
Номер
24(29), С. 5281 - 5286
Опубликована: Июль 18, 2022
A
Ru(II)-catalyzed
decarbonylative
alkylation
and
annulation
of
salicylaldehydes
2-aminobenzaldehydes
with
iodonium
ylides
has
been
developed
for
the
synthesis
dibenzo[b,d]furans
NH-free
carbazolones.
The
reaction
proceeds
smoothly
under
mild
conditions
a
low
catalyst
loading
broad
substrate
compatibility.
Notably,
hydroxy
free
amino
groups
were
demonstrated
to
be
effective
directing
groups,
enabling
successful
aldehyde
C–H
bond
activation
subsequent
decarbonylation
inexpensive
Ru(II)
catalyst.
