Asian Journal of Organic Chemistry,
Год журнала:
2022,
Номер
11(8)
Опубликована: Июнь 16, 2022
Abstract
Indoles
are
extremely
important
and
versatile
building
blocks
in
the
field
of
chemistry.
This
review
highlights
advance
made
three‐component
reactions
indoles
between
2011–2021.
The
reaction
types
classified
into
three
categories
based
on
trigger
mechanisms.
Reactions
with
alkenes,
alkynes,
aldehydes,
imines,
ketones,
S,
Se,
etc
discussed.
In
order
to
highlight
mechanisms
involved,
this
has
provided
specific
analysis
inside
a
gray
box
each
scheme.
We
hope
these
studies
will
promote
future
research
indole
area.
Chemical Society Reviews,
Год журнала:
2024,
Номер
53(10), С. 4926 - 4975
Опубликована: Янв. 1, 2024
In
search
for
the
perfect
wave(length).
This
review
is
dedicated
to
recent
efforts
in
development
of
visible
light
driven
photochemical
strategies
occurring
coloured
organic
compounds.
ACS Catalysis,
Год журнала:
2022,
Номер
12(21), С. 13282 - 13291
Опубликована: Окт. 17, 2022
Chiral
acyclic
all-carbon
quaternary
stereocenters
are
widely
present
in
natural
products
and
pharmaceuticals.
However,
their
introduction
remains
a
challenging
topic
the
synthetic
research
community.
Here,
we
report
an
efficient
metal-free
method
for
construction
of
chiral
centers
sited
at
α-position
aldehyde
or
ketone
moiety.
This
is
achieved
via
well-designed
reaction
cascade
involving
arylalkynes,
benzoquinones,
electron-rich
(hetero)arenes
use
visible
light
phosphoric
acid
catalysis.
Notably,
asymmetric
catalytic
visible-light-induced
Paternò–Büchi
cycloaddition/electrocyclic
ring-opening/α-selective
arylation
α,β-unsaturated
carbonyl
compound
cascades
achieved.
Moreover,
works
well
broad
range
these
three
components
(>70
examples).
Furthermore,
rich
chemistry
embedded
provides
variety
synthetically
useful
building
blocks
that
otherwise
difficult
to
access.
Lastly,
origin
enantioselectivity
was
investigated
by
density
functional
theory,
revealing
CH/π
interactions
play
crucial
role
stereocontrol
reaction.
Alkynes
represent
a
family
of
pivotal
and
sustainable
feedstocks
for
various
industries
such
as
pharmaceuticals,
agrochemicals,
materials,
they
are
widely
used
important
starting
materials
the
production
broad
range
chemical
entities.
Nevertheless,
efficient
structural
elaborations
alkynes
in
synthesis,
especially
asymmetric
multifunctionalization
alkynes,
remain
largely
unexplored.
It
is
thus
imperative
to
develop
new
synthetic
approaches,
making
use
these
richly
available
feedstocks,
enabling
their
conversion
value-added
chiral
molecules.
Here,
we
disclose
our
findings
on
highly
enantioselective
by
merging
photochemistry
phosphoric
acid
catalysis.
Our
reported
one-pot
protocol
applicable
all
types
alkyne
substrates,
incorporating
three
reactants
fully
atom-economic
fashion
produce
optically
enriched
tetrasubstituted
triaryl-
diarylmethanes,
scaffolds
medicinal
chemistry
biological
sciences.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(21), С. 3556 - 3571
Опубликована: Авг. 2, 2023
Abstract
Harnessing
visible
light
to
trigger
(aza
and
thia)
Paternò‐Büchi
reaction
injects
new
vitality
into
[2+2]
photocyclization
enable
impressive
reactivity
modes.
The
popular
is
one
of
the
most
efficient
ways
synthesize
strained
four‐membered
heterocycles.
Recently,
visible‐light‐triggered
reactions
have
received
considerable
attentions
as
this
strategy
has
overcome
some
long‐standing
challenges,
remarkable
achievements
been
made
within
field.
Strained
heterocyclics
with
favorable
properties
provide
a
perfect
combination
stable
skeletons
for
pharmaceutical
chemistry
intermediates
further
transformation.
In
review,
we
highlight
recent
advances
in
an
emphasis
on
mechanism
applications.
Organization
review
follows
subdivision
according
type
substrate
classes.
Green Chemistry,
Год журнала:
2024,
Номер
26(5), С. 2705 - 2711
Опубликована: Янв. 1, 2024
A
novel
synthetic
strategy
to
access
strained
heterocycles
is
revealed
through
photocatalysed
annulative
formal
4-
endo-dig
cyclization
of
propargyl
alcohols/amines
with
benzoquinones
under
catalyst/reagent-free
conditions
using
non-hazardous
solvent.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(3), С. 1669 - 1680
Опубликована: Янв. 11, 2024
A
mild
and
eco-friendly
visible-light-induced
protocol
for
the
hydroacylation
of
quinones
with
α-keto
acids
has
been
developed.
In
absence
any
catalyst
or
additive,
decarboxylative
proceeded
smoothly
under
visible-light
irradiation
at
room
temperature.
wide
range
were
well-tolerated
afforded
products
up
to
88%
isolated
yield.
The
reaction
can
be
scaled
up,
induced
groups
are
useful
further
synthetic
applications.
Preliminarily,
mechanistic
studies
indicated
that
photoactive
absorb
visible
light
facilitate
transformation.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(6), С. 892 - 899
Опубликована: Фев. 28, 2023
Visible
light
induced
activation
of
para-benzoquinone,
and
its
sequential
coupling
with
alkynes
ortho-phenylenediamines/ortho-aminophenols
is
reported.
The
protocol
provides
a
route
for
synthesizing
value-added
quinoxaline
derivatives
tetrasubstituted
carbon
stereocenter
at
room
temperature
in
36–75%
yields.
Mechanistic
investigation
suggests
that
the
reaction
proceeds
via
in-situ
generation
para-quinone
methide
through
direct
excitation
para-benzoquinone
blue
light.
As
service
to
our
authors
readers,
this
journal
supporting
information
supplied
by
authors.
Such
materials
are
peer
reviewed
may
be
re-organized
online
delivery,
but
not
copy-edited
or
typeset.
Technical
support
issues
arising
from
(other
than
missing
files)
should
addressed
Please
note:
publisher
responsible
content
functionality
any
Any
queries
content)
directed
corresponding
author
article.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(30), С. 6174 - 6179
Опубликована: Янв. 1, 2023
Simple
irradiation
of
quinones
and
alkynes
with
blue
light
is
sufficient
to
trigger
[2
+
2]
photocycloadditions
giving
rise
either
fused
cyclobutenes
or
reactive
para
-quinone
methides
depending
on
the
quinone
structure.
Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(22)
Опубликована: Март 9, 2023
Abstract
A
simple
visible‐light‐induced
CuCl‐catalyzed
synthesis
was
developed
for
highly
functionalized
carbon‐centered
compounds
(α‐alk/aryloxy‐α‐diaryl/alkylaryl‐acetaldehydes/ketones)
at
room
temperature
using
benzoquinone,
alkyl/aryl
alcohol,
and
terminal/internal
alkynes.
Late‐stage
show
good
antifungal
activities,
especially
against
Candida
krusei
fungal
strain,
in
vitro
experiments
(the
Broth
microdilution
method).
Moreover,
toxicity
tests
(zebrafish
egg
model
experiments)
indicated
that
these
had
negligible
cytotoxicity.
The
green
chemistry
metrics
(E‐factor
value
is
7.3)
eco‐scale
(eco‐scale
58.8)
evaluations
the
method
simple,
mild,
efficient,
eco‐friendly,
environmentally
feasible.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(30), С. 6218 - 6224
Опубликована: Янв. 1, 2023
Herein,
we
demonstrate
a
redox-neutral,
operationally
simple,
atom-economical,
and
additive-free
approach
for
the
synthesis
of
indolyl
diarylmethanes
via
radical
reaction
indoles
with
para-quinone
methides
(p-QMs)
under
visible-light
mediated
conditions
using
eosin
Y
as
an
organophotoredox
catalyst.
This
protocol
was
found
to
be
compatible
wide
range
differently
substituted
p-QMs
in
organic
well
aqueous
media
irradiation,
furnishing
desired
products
good
excellent
yields.
