Organic Letters,
Год журнала:
2019,
Номер
21(13), С. 5363 - 5367
Опубликована: Июнь 26, 2019
Pyridones
are
important
heteroaromatic
scaffolds
found
in
natural
products
and
pharmaceuticals
are,
therefore,
of
major
interest
organic
synthetic
chemistry.
Here
we
report
the
first
C–H
pyridonation
unactivated
(hetero-)arenes,
providing
a
methodology
to
directly
access
N-aryl-2-
4-pyridones.
Generation
pyridinium
radical
cations
through
single-electron
reduction
allows
for
synthesis
pyridones
on
structurally
complex
molecules.
Molecules,
Год журнала:
2020,
Номер
25(3), С. 505 - 505
Опубликована: Янв. 24, 2020
Focusing
on
the
literature
progress
since
2002,
present
review
explores
highly
significant
role
that
multicomponent
reactions
(MCRs)
have
played
as
a
very
important
tool
for
expedite
synthesis
of
vast
number
organic
molecules,
but
also,
highlights
fact
many
such
molecules
are
biologically
active
or
at
least
been
submitted
to
any
biological
screen.
The
selected
papers
covered
in
this
must
meet
two
mandatory
requirements:
(1)
reported
products
should
be
obtained
via
reaction;
(2)
actives
tested
property.
Given
diversity
synthetic
approaches
utilized
MCRs,
diverse
nature
activities
evaluated
synthesized
compounds,
and
considering
their
huge
structural
variability,
much
data
organized
into
concise
schemes
tables
facilitate
comparison,
underscore
key
points
review.
Journal of the American Chemical Society,
Год журнала:
2018,
Номер
140(13), С. 4489 - 4493
Опубликована: Март 15, 2018
Annulated
pyridones
are
an
important
scaffold
found
in
many
biologically
active
compounds.
A
Ni(0)-catalyzed
C–H
functionalization
of
2-
and
4-pyridones
is
disclosed,
providing
access
to
annulated
via
enantioselective
intramolecular
olefin
hydroarylation.
Key
the
success
transformation
was
development
a
sterically
hindered
tunable
N-heterocyclic
carbene
ligand
resembling
chiral
version
IPr.
This
allows
for
mild
reaction
temperatures,
leads
excellent
yields
enantioselectivities.
Organic Chemistry Frontiers,
Год журнала:
2020,
Номер
7(12), С. 1527 - 1569
Опубликована: Янв. 1, 2020
Heterocyclic
alkenes
and
their
derivatives
are
an
important
class
of
reactive
feedstock
valuable
synthons.
This
review
highlights
the
transition-metal-catalyzed
coupling
heterocyclic
alkenesviaa
C–H
functionalization
strategy.
Angewandte Chemie International Edition,
Год журнала:
2019,
Номер
58(43), С. 15244 - 15248
Опубликована: Авг. 1, 2019
An
efficient
visible
light
induced
rhodium(I)-catalyzed
regioselective
borylation
of
aromatic
C-H
bonds
is
reported.
The
photocatalytic
system
based
on
a
single
NHC-RhI
complex
capable
both
harvesting
and
enabling
the
bond
breaking/forming
at
room
temperature.
chelating
nature
NHC-carboxylate
ligand
was
critical
to
ensure
stability
RhI
provide
excellent
activities.
Experimental
mechanistic
studies
evidenced
photooxidative
ortho
addition
upon
irradiation
with
blue
LEDs,
leading
cyclometalated
RhIII
-hydride
intermediate.
Angewandte Chemie International Edition,
Год журнала:
2020,
Номер
59(30), С. 12534 - 12540
Опубликована: Июнь 2, 2020
C7-H-functionalized
indoles
are
ubiquitous
structural
units
of
biological
and
pharmaceutical
compounds
for
numerous
antiviral
agents
against
SARS-CoV
or
HIV-1.
Thus,
achieving
site-selective
functionalizations
the
C7-H
position
indoles,
while
discriminating
among
other
bonds,
is
in
high
demand.
Herein,
we
disclose
activations
by
ruthenium(II)
biscarboxylate
catalysis
under
mild
conditions.
Base-assisted
internal
electrophilic-type
substitution
C-H
ruthenation
weak
O-coordination
enabled
functionalization
offered
a
broad
scope,
including
C-N
C-C
bond
formation.
The
versatile
ruthenium-catalyzed
were
characterized
gram-scale
syntheses
traceless
removal
directing
group,
thus
providing
easy
access
to
pharmaceutically
relevant
scaffolds.
Detailed
mechanistic
studies
through
spectroscopic
spectrometric
analyses
shed
light
on
unique
nature
robust
ruthenium
indoles.
Re-catalyzed
highly
regio-
and
stereoselective
o-C(sp2)–H
silylalkenylation
of
arenes
is
reported
using
a
directing
group
approach
under
ligand-,
additive-,
base-free
conditions.
A
series
imine
groups
(DGs)
have
been
exploited
on
aromatic
aldehydes
to
overcome
de
novo
synthesis.
This
unique
protocol
allows
us
access
o-C–H
activation
various
heterocyclic
moieties,
including
N-aryl
2-pyridones
arylpyridines.
Sequential
difunctionalization
experiments
performed.
mechanistic
carried
out
gain
insight.
European Journal of Organic Chemistry,
Год журнала:
2018,
Номер
2018(44), С. 6068 - 6082
Опубликована: Июнь 1, 2018
C–H
activation
has
emerged
as
a
viable
alternative
to
traditional
C–C
bond
forming
reactions
such
the
Suzuki–Miyaura,
Stille,
Negishi
and
others.
However,
is
rarely
employed
in
total
synthesis
or
fine
chemical
manufacture,
particularly
an
end‐game
strategy.
This
may
be
due
harsh
conditions
typically
required.
For
become
truly
useful
versatile
methodology,
must
emerge
which
are
applicable
compounds
with
multiple
functionalities.
In
this
review,
we
hope
inspire
chemistry
community
focus
their
efforts
on
milder
for
cross‐dehydrogenative
coupling.
To
end,
have
focused
describing
it
been
applied
several
classes
of
biologically
interesting,
but
chemically
sensitive
motifs:
2‐pyrones,
2‐pyridones,
2‐coumarins
2‐quinolones.
Angewandte Chemie International Edition,
Год журнала:
2019,
Номер
58(16), С. 5338 - 5342
Опубликована: Фев. 12, 2019
Complexity-increasing
Domino
reactions
comprising
C-H
allenylation,
a
Diels-Alder
reaction,
and
retro-Diels-Alder
reaction
were
realized
by
versatile
catalyst
derived
from
earth-abundant,
non-toxic
manganese.
The
activation/Diels-Alder/retro-Diels-Alder
alkyne
annulation
sequence
provided
step-economical
access
to
valuable
indolone
alkaloid
derivatives
through
facile
organometallic
activation
manifold
with
transformable
pyridines.
