Chemical Society Reviews,
Год журнала:
2021,
Номер
50(20), С. 11249 - 11269
Опубликована: Янв. 1, 2021
The
site-selective
C-H
bond
functionalization
of
heteroarenes
can
eventually
provide
chemists
with
great
techniques
for
editing
and
building
complex
molecular
scaffolds.
During
the
past
decade,
benzo-fused
N-heterocycles
such
as
indoles
quinolines
have
been
among
most
widely
investigated
organic
templates.
Early
developments
led
to
on
pyrrole
pyridine
cores
quinolines;
however,
benzenoid
ring
has
remained
a
challenge
in
catalysis.
In
this
review,
we
elaborate
recent
highly
challenging
bonds
less-reactive
core
quinolines.
These
findings
are
mainly
described
selective
directing
group
assisted
strategies,
remote
their
reaction
mechanisms.
underlying
principle
each
strategy
is
elucidated,
which
aims
facilitate
design
more
advanced
structure
heterocycles
based
bioactive
molecules,
synthetic
drugs,
material
aspects.
Moreover,
challenges
perspectives
catalytic
access
arene
backbone
also
proposed
conclusion
section.
Asian Journal of Organic Chemistry,
Год журнала:
2019,
Номер
8(11), С. 1949 - 1969
Опубликована: Март 13, 2019
Abstract
Maleimide
and
succinimide
core
moieties
are
present
in
various
natural
products
pharmaceuticals.
In
addition,
these
derivatives
can
be
readily
modified
into
biologically
important
organic
molecules
including
pyrrolidines
γ‐lactams.
A
transition‐metal‐catalyzed
chelation‐assisted
functionalization
of
inert
C−H
bond
with
electrophiles
or
nucleophiles
is
one
the
efficient
methods
to
construct
chemical
bonds
a
highly
atom‐
step‐economical
manner.
The
review
describes
recent
advances
reaction
involving
maleimides
by
activation
methodology.
having
directing
groups,
such
as
ketone,
acyl,
pyridyl,
pyrimidyl,
oxime,
amide,
imidate,
chromone,
azo,
N
‐sulfonyl
ketimine,
carboxylic
acids,
aldimines,
were
described.
scope,
limitation
mechanistic
investigation
alkylation,
annulation
alkenylation
reactions
discussed
elaborately.
This
article
includes
entire
report
on
bond‐forming
strategy
until
end
2018.
Organic Letters,
Год журнала:
2019,
Номер
21(18), С. 7189 - 7193
Опубликована: Сен. 4, 2019
A
dehydrogenative
annulation
of
2-arylindazoles
with
maleimides
for
the
switchable
synthesis
indazolo[2,3-a]pyrrolo[3,4-c]quinolinones
or
spiroindolo[1,2-b]indazole-11,3′-pyrrolidinones
is
presented.
Mechanistically,
formation
title
compounds
involves
a
Rh(III)-catalyzed
C–H
metalation
2-arylindazole,
followed
by
maleimide
insertion
and
intramolecular
cyclization.
Interestingly,
selectivity
to
form
fused
spiro
could
be
switched
resorting
different
additives.
The
notable
features
this
protocol
include
simple
substrates
excellent
atom
economy
regioselectivity.
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.
New Journal of Chemistry,
Год журнала:
2021,
Номер
45(31), С. 13692 - 13746
Опубликована: Янв. 1, 2021
This
review
summarises
a
wide
range
of
transformations
on
the
indole
skeleton,
including
arylation,
alkenylation,
alkynylation,
acylation,
nitration,
borylation,
and
amidation,
using
transition-metal
catalyzed
C–H
functionalization
as
key
step.
Organic Letters,
Год журнала:
2019,
Номер
21(4), С. 1068 - 1072
Опубликована: Янв. 28, 2019
A
Co(III)-catalyzed
novel
[4
+
2]
annulation
of
N-chlorobenzamides
with
maleimides
has
been
reported.
Mostly,
are
known
to
furnish
the
Michael-type
or
1,1-type
cyclized
products
while
treating
amides.
In
this
reaction,
furnished
annulated
in
good
yields
at
room
temperature
being
treated
internal
oxidizing
N-chlorobenzamide
as
a
directing
group.
The
developed
methodology
is
compatible
variety
functional
groups.
obtained
featured
some
biologically
active
molecules.
Organic Letters,
Год журнала:
2019,
Номер
21(5), С. 1320 - 1324
Опубликована: Фев. 14, 2019
A
versatile
and
site-selective
rhodium(III)-catalyzed
aerobic
oxidative
alkenylation
of
arylacetamides
including
primary,
secondary,
tertiary
amides
having
a
weak
O-coordinating
acetamide
directing
group
with
alkenes
is
described.
In
the
reaction,
air
was
utilized
as
sole
oxidant.
The
reaction
compatible
activated
maleimides.
The Journal of Organic Chemistry,
Год журнала:
2019,
Номер
84(7), С. 4058 - 4071
Опубликована: Фев. 27, 2019
An
Rh(III)-catalyzed
1,1-cyclization
of
N-methoxy
benzamides
with
maleimides
providing
isoindolinone
spirosuccinimides
through
N–H/C–H/N–O
bond
activation
is
described.
The
detailed
mechanistic
investigation
including
isolation
key
metalacycle
intermediate,
deuterium
labeling
studies,
and
DFT
calculations
were
performed.
computational
study
reveals
that
the
AcOH
formed
in
reaction
medium
plays
a
role
N–OMe
cleavage
oxidation
Rh(I)
to
Rh(III).
Organic Letters,
Год журнала:
2019,
Номер
21(12), С. 4525 - 4530
Опубликована: Июнь 10, 2019
A
weakly
coordinating
carboxylate
directing
group
assisted
C–H
activation
with
maleimides
leading
to
novel
and
switchable
decarboxylative
Heck-type
[4
+
1]
annulation
products
catalyzed
by
Rh(III)
has
been
reported.
In
these
reactions,
solvents
play
a
vital
role
in
switching
the
selectivity.
An
aprotic
solvent,
THF,
leads
product
while
protic
TFE,
results
product.
The
methodology
shows
high
functional
tolerance.
Organic Letters,
Год журнала:
2018,
Номер
20(22), С. 6998 - 7002
Опубликована: Окт. 29, 2018
Functionalization
of
the
indole
N–H
bond
for
enantioselective
synthesis
biologically
important
pyrroloquinoline
derivatives
has
been
reported
under
oxidative
N-heterocyclic
carbene
catalysis
conditions.
The
interception
catalytically
generated
chiral
α,β-unsaturated
acylazoliums
with
proceeds
in
an
aza-Michael/Michael/lactonization
sequence
to
deliver
good
yields,
diastereoselectivities,
and
enantioselectivities.
simultaneous
enhancement
reactivity
selectivity
observed
polar
aprotic
solvents
is
noteworthy.
