Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(28), P. 5034 - 5039
Published: July 7, 2022
Direct
formylation
of
feedstock
indoles
with
newly
developed,
cost-effective
deuterated
glyoxylic
acid
as
agent
under
visible
light
and
air
(O2)
terminal
oxidant
has
been
developed.
An
isatin
byproduct
produced
from
the
corresponding
indole
reactant
serves
a
facilitator
for
process.
The
simple,
mild,
metal-
oxidant-free
protocol
enables
synthesis
structurally
diverse
C1-deuterated
3-formylindoles
broad
functional
group
tolerance
late-stage
functionalization
at
high
level
D-incorporation
(95–99%).
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(3), P. 1846 - 1857
Published: Jan. 12, 2024
Herein,
we
describe
an
efficient
transition-metal-free
regioselective
C3alkylation
of
indoles
for
the
synthesis
bis(indolyl)methanes
and
3-styryl
indoles.
Nitrobenzene
is
employed
as
oxidant
to
oxidize
alcohols
in
presence
a
strong
base
reaction
avoids
use
transition
metals
such
Ru
Mn.
The
protocol
provides
favorable
route
access
biologically
active
compounds
arundine,
vibrindole
A,
turbomycin
B.
Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
29(32)
Published: March 21, 2023
Abstract
In
recent
years,
the
synthesis
of
C‐aryl
glycosides
hrough
C−H
functionalization
has
attracted
extensive
attention
organic
chemists
due
to
its
steps
and
atomic
economy.
this
concept,
we
systematically
summarizes
with
diverse
regioselectivity
diastereoselectivity
from
perspective
arylation
glycosylation
arenes.
It
can
be
found
that
a
series
recently
developed
reactions
have
higher
site‐selectivity
diastereomeric
selectivity
than
Friedel–Crafts
reaction.
The
reaction
conditions
are
milder,
which
compatible
acid‐sensitive
protective
groups,
such
as
acetals
or
ketals,
deprotection
is
more
convenient.
seen
there
few
reports
on
remote
aromatic
hydrocarbons,
new
field
needs
further
research.
addition,
lot
shortcomings,
need
explored:
a)
precise
regulation
stereoselectivity
in
process
also
optimization;
b)
research
mechanism
almost
limited
DFT
calculation,
no
exact
experimental
evidence.
For
key
parts,
specific
between
cyclo‐metal
intermediates
glycosyl
donors
ortho
‐C
Ar
−H
still
unclear;
c)
fact
aryl
glycoside
compounds
contain
bare
hydroxyl
groups
practical
applications,
it
an
urgent
problem
realize
compatibility
substrates
containing
naked
remove
by
mild
efficient
method
after
reaction;
d)
rapidly
developing
field,
study
greener,
economical
arenes
future,
will
conducive
biological
application
significance.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(2), P. 1193 - 1204
Published: Jan. 9, 2024
Herein,
the
C3–H
alkylation
of
2H-indazoles
and
indoles
with
sulfoxonium
ylides
is
developed
under
visible-light
photocatalysis.
This
protocol
employs
easily
accessible
reagents,
a
wide
range
2H-indazoles,
indoles,
are
suitable
for
this
reaction
to
afford
desired
products
benign
conditions.
Synergistic
experimental
computational
studies
suggest
that
involving
photocatalysis
could
proceed
via
different
mechanistic
pathways.
For
C3-alkylation
triplet
energy
transfer
pathway
proposed
quenching
excited
photocatalyst.
Subsequently,
formed
state
undergo
radical
attack
on
C═S
moiety
ylides.
After
dissociation
DMSO
1,2-H
migration,
final
product
be
yielded.
However,
such
not
applicable
indoles.
Instead,
converted
C-centered
in
presence
KH2PO4
photoredox
The
can
C3-site
thus
lead
Chemical Communications,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
A
red-light
(
λ
=
640
nm)-mediated
C-3
formylation
of
indoles
utilizing
a
helical
carbenium
ion
as
photocatalyst
and
2,2-dimethoxy-
N
,
-dimethylethanamine
formylating
source
is
presented.
Chemistry - An Asian Journal,
Journal Year:
2020,
Volume and Issue:
15(24), P. 4184 - 4198
Published: Nov. 9, 2020
Selective
editing
of
the
benzenoid
C-H
bonds
(C4-C7)
in
indoles/indolines
has
received
great
interest
because
functionalized
are
featured
many
marketed
drugs
and
natural
products.
Transition-metal-catalyzed
directed
functionalization
thus
been
developed
to
manipulate
core
through
C-C
C-heteroatom
bond
formation.
This
review
covers
recent
advances
selective
forming
reactions,
alkylation,
alkenylation
alkynylation,
over
ring
using
metal
catalysis.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(34), P. 4613 - 4616
Published: Jan. 1, 2024
We
report
an
innovative
synthetic
strategy
for
the
generation
of
polysubstituted
indoles
from
indolines,
aryldiazonium
salts,
and
azoles.
The
methodology
encompasses
electrophilic
substitution
reaction
affording
C5-indoline
intermediates
which
undergo
iodine-mediated
oxidative
transformation
coupled
with
C-H
functionalization
to
yield
indole
derivatives.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
87(2), P. 1056 - 1064
Published: Dec. 29, 2021
An
electrochemical
cross-dehydrogenative
coupling
of
indoles
with
xanthenes
has
been
established
at
room
temperature.
This
reaction
could
proceed
in
the
absence
any
catalyst
or
external
oxidant,
and
generate
indole
derivatives
moderate
yields.
Mechanistic
experiments
support
that
a
radical
pathway
maybe
involved
this
system.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(15), P. 5983 - 5987
Published: July 23, 2021
An
electrochemical
approach
for
the
site-selective
C–H
cyanation
of
indoles
employing
readily
available
TMSCN
as
cyano
source
has
been
developed.
The
electrosynthesis
relies
on
tris(4-bromophenyl)amine
a
redox
catalyst,
which
achieves
better
yield
and
regioselectivity.
A
variety
C2-
C3-cyanated
were
obtained
in
satisfactory
yields.
reactions
are
conducted
simple
undivided
cell
at
room
temperature
obviate
need
transition-metal
reagent
chemical
oxidant.
Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
364(4), P. 838 - 844
Published: Dec. 17, 2021
Abstract
A
convenient
and
effective
method
of
ruthenium‐catalyzed
C−H/N−H
annulations
using
vinylene
carbonate
as
oxidizing
acetylene
surrogate
has
been
disclosed.
This
is
scalable
compatible
with
a
wide
range
functional
groups,
providing
step‐economical
access
to
indole
synthesis
Preliminary
mechanistic
studies
provided
support
for
reversible,
acetate‐assisted
C−H
ruthenation,
along
subsequent
olefin
insertion.
magnified
image
