The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(23), P. 16867 - 16881
Published: Nov. 1, 2021
Transamidation
reactions
are
often
mediated
by
reactive
substrates
in
the
presence
of
overstoichiometric
activating
reagents
and/or
transition
metal
catalysts.
Here
we
report
use
CO2
as
a
traceless
catalyst:
catalytic
amounts
CO2,
transamidation
were
accelerated
with
primary,
secondary,
and
tertiary
amide
donors.
Various
amine
nucleophiles
including
amino
acid
derivatives
tolerated,
showcasing
utility
peptide
modification
polymer
degradation
(e.g.,
Nylon-6,6).
In
particular,
N,O-dimethylhydroxyl
amides
(Weinreb
amides)
displayed
distinct
reactivity
CO2-catalyzed
versus
N2
atmosphere.
Comparative
Hammett
studies
kinetic
analysis
conducted
to
elucidate
activation
mechanism
molecular
which
was
supported
DFT
calculations.
We
attributed
positive
effect
reaction
stabilization
tetrahedral
intermediates
covalent
binding
electrophilic
CO2.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(19), P. 3918 - 3941
Published: Jan. 1, 2023
This
review
demonstrates
the
redox-neutral
synthetic
approaches
towards
valuable
heterocycles
such
as
isoquinolines,
indoles,
isoquinolones,
and
tetrahydroquinolines
via
high-valent
Cp*Co(
iii
)
catalysis.
Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(8)
Published: July 21, 2023
Abstract
The
alkali
metal
tert
‐butoxides
have
found
wide
application
as
catalysts
and
activators
for
the
conversion
of
numerous
organic
molecules.
These
formidable
additives
in
catalytic
amounts
are
extensively
employed
transition
metal‐free
approaches
to
serve
single‐electron
transfer
processes
towards
formation
C−C
C‐heteroatom
bond
formation.
This
review
elucidates
their
multifaceted
roles
encompassing
a
series
novel
synthetic
methodologies,
in‐depth
analyses
reactivity
patterns,
efficiencies
across
myriad
reactions.
involvement
either
directly
or
combination
with
other
metals
discussed
along
detailed
mechanistic
pathways
various
Overall,
this
article
summarises
approximately
all
reactions
those
been
influenced
by
reported
last
decades.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(18), P. 3206 - 3209
Published: May 4, 2023
Isoquinoline
is
a
privileged
structure
in
many
bioactive
compounds
and
valuable
ligands.
Transition-metal-catalyzed
oxidative
annulation
of
imine
derivatives
has
become
promising
synthetic
method;
however,
catalytic
synthesis
3,4-nonsubstituted
isoquinolines
by
formal
acetylene
been
scarce
to
date.
Herein,
we
introduce
vinyl
selenone
as
an
effective
surrogate
for
the
Rh-catalyzed
annulative
coupling
under
mild
conditions.
The
Se
fragment
can
be
recovered
diselenide
recycled.
product
readily
converted
1-aminoisoquinolines.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(43), P. 7878 - 7883
Published: Oct. 23, 2023
We
have
developed
a
Cp*Co(III)-catalyzed
reverse
regioselective
[4
+
2]
annulation
of
N-chlorobenzamides/acrylamides
with
vinylsilanes
for
the
synthesis
4-silylated
isoquinolones.
The
reaction
was
performed
at
ambient
temperature
under
redox-neutral
conditions.
utilized
N-Cl
bond
as
an
internal
oxidant,
furnished
required
products
excellent
regioselectivities,
and
demonstrated
high
functional
group
tolerance.
synthetic
utility
isoquinolones
has
been
preparation
4-heteroarylated
4-alkylated
via
metal-free
C-C
couplings.
Additionally,
3,4-dihydroisoquinolones
were
synthesized
protodesilylation
isoquinolones,
thus
making
vinylsilane
ethylene
surrogate.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(2), P. 1235 - 1240
Published: Jan. 9, 2024
Alkaline-metal-promoted
divergent
syntheses
of
1-aminoisoquinolines
and
isoquinolines
have
been
reported
involving
2-methylaryl
aldehydes,
nitriles,
LiN(SiMe3)2
as
reactants.
In
addition,
the
three-component
reaction
has
developed
to
furnish
1-aminoisoquinolines.
This
protocol
features
readily
available
starting
materials,
excellent
chemoselectivity,
broad
substrate
scope,
satisfactory
yields.
ACS Catalysis,
Journal Year:
2025,
Volume and Issue:
15(3), P. 1596 - 1606
Published: Jan. 14, 2025
Transition
metal-catalyzed
reductive
coupling
chemistry
has
been
recognized
as
a
powerful
tool
for
the
synthesis
of
diverse
organic
molecules.
However,
despite
enormous
progress
in
this
field,
there
is
no
precedent
tandem
widely
accessible
nitriles
with
electrophiles
that
contain
σ-
and
π-type
(σ/π-type)
electrophilic
functional
groups
simultaneously.
Herein,
we
have
established
unique
cobalt
catalysis
system,
enabling
chemoselective
coupling/tandem
cyclization
reaction
aryl
halides
(Br,
Cl,
I)
bearing
carbonyl
moiety
variety
aryl,
alkenyl,
alkyl
via
carbocobaltation
unknown
yet.
The
protocol
allows
modular
structurally
isoquinolines
wide
substrate
scope
(>60
examples),
good
functionalities
tolerance,
chemoselectivity.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(16), P. 6578 - 6582
Published: Aug. 11, 2021
An
efficient
palladium-catalyzed
reaction
of
N-propargyl
oxazolidines
for
the
construction
4-substituted
isoquinolines
under
microwave
irradiation
is
developed.
This
transformation
proceeds
through
a
sequential
reductive
cyclization/ring-opening/aromatization
cascade
via
C–O
and
C–N
bond
cleavages
oxazolidine
ring.
The
practical
value
this
method
has
also
been
explored
by
conducting
millimole-scale
reaction,
as
well
transforming
isoquinoline
into
key
intermediate
synthesis
lamellarin
analogue.
ChemistrySelect,
Journal Year:
2024,
Volume and Issue:
9(3)
Published: Jan. 17, 2024
Abstract
Organic
synthesis
involves
the
production
of
important
chemical
structures
using
scalable
and
cost‐effective
methods
that
are
also
environmentally
friendly.
In
this
review,
a
detailed
analysis
use
iodine
DMSO
in
various
synthetic
routes
for
preparation
valuable
targets
presented.
These
reduce
acceptance
on
expensive
additives
reagents,
offer
more
sustainable
solution
these
scaffolds.
