Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(20), С. 3600 - 3606
Опубликована: Июль 27, 2022
Abstract
A
strategy
for
the
synthesis
of
quinazolines
via
elemental
sulfur‐mediated
oxidative
condensation
nitriles
and
2‐(aminomethyl)anilines
was
developed.
The
reaction
carried
out
under
metal‐/solvent‐free
conditions,
tolerates
a
wide
range
functional
groups
to
provide
corresponding
products
in
56%‐91%
yield,
can
be
performed
on
gram‐scale.
UV/Vis
absorption
fluorescence
spectra
several
product
derivatives
were
measured
study
their
photophysical
properties.
magnified
image
Organic Letters,
Год журнала:
2024,
Номер
26(22), С. 4835 - 4839
Опубликована: Май 29, 2024
A
three-component
cascade
reaction
involving
cyclohexanones,
anilines,
and
diaryl
diselenides
under
metal-free
conditions
is
reported.
The
ortho-selenation
of
cyclohexanones
with
diselenides,
followed
by
sequential
dehydroaromatization
enables
the
preparation
a
variety
o-selanyl
anilines
in
moderate
to
excellent
yields.
This
innovative
transformation
notable
for
its
tolerance
functional
groups
suitable
late-stage
modification
complex
pharmaceuticals.
ACS Catalysis,
Год журнала:
2019,
Номер
10(1), С. 154 - 159
Опубликована: Ноя. 27, 2019
Radical
addition
is
a
robust
tool
for
bond
formation.
While
ketyl
radical
reactivity
of
aldehydes
by
photoredox
has
been
well-established,
herein,
we
have
now
revealed
pathway
umpolung
with
or
without
external
reductant.
Hence,
the
reductive
alkylations
and
challenging
benzylations
nitrogen
heteroarenes
(i.e.,
Minisci
reactions)
are
enabled
bromide-promoted
visible
light-mediated
photocatalysis.
The
present
protocol
offers
mild,
viable
method
late-stage
transition-metal-free
biologically
active
nitrogen-heteroarene
molecules.
Mechanistic
studies
indicative
bromide-initiated
acyl
mechanism
in
absence
Accounts of Chemical Research,
Год журнала:
2020,
Номер
53(10), С. 2395 - 2413
Опубликована: Сен. 17, 2020
ConspectusTransition-metal-catalyzed
cross-coupling
reactions
represent
one
of
the
most
straightforward
and
efficient
protocols
to
assemble
two
different
molecular
motifs
for
construction
carbon–carbon
or
carbon–heteroatom
bonds.
Because
their
importance
wide
applications
in
pharmaceuticals,
agrochemicals,
materials,
etc.,
have
been
well
recognized
2010
Nobel
Prize
chemistry.
However,
classical
transition-metal-catalyzed
(e.g.,
Suzuki–Miyaura,
Buchwald–Hartwig,
Ullmann
reactions),
organohalides,
which
mainly
stem
from
nonrenewable
fossil
resources,
are
often
utilized
as
coupling
partners
with
halide
wastes
being
generated
after
reactions.
To
make
more
sustainable,
we
initiated
a
general
research
program
by
employing
phenols
cyclohexa(e)nones
(the
reduced
forms
phenols)
pivotal
feedstocks
(coupling
partners),
instead
commonly
used
fossil-derived
build
C–O,
C–N,
C–C
Phenols
(cyclohexa(e)nones)
widely
available
can
be
obtained
lignin
biomass,
highlighting
renewable
sustainable
features.
Moreover,
water
is
expected
only
stoichiometric
byproduct,
thus
avoiding
wastes.Notably,
utilizing
phenols/cyclohexa(e)nones
not
based
on
traditional
"oxidative-addition
reductive-elimination"
mechanism,
but
via
novel
"phenol-cyclohexanone"
redox
couple.
This
new
working
mechanism
opens
up
horizons
designing
simple
nucleophilic
addition
cyclohexanones
along
aromatization
processes,
thereby
simplifying
design
laborious
optimization
transition-metal
precursors
Pd,
Ni,
Cu,
etc.),
ligands
Specifically,
this
Account,
will
summarize
discuss
our
related
work
following
three
categories:
"formal
oxidative
couplings
cyclohexa(e)nones",
reductive
phenols",
redox-neutral
phenols".
The
successes
these
projects
clearly
demonstrated
initial
inspirations
rational
designs
develop
without
"conventional
conditions"
pushing
reaction
frontiers
cyclohexanones,
ultimately,
phenol
targets.
Advanced Synthesis & Catalysis,
Год журнала:
2020,
Номер
362(18), С. 3795 - 3823
Опубликована: Май 18, 2020
Abstract
The
synthetic
methodology
for
direct
indole
functionalizations
is
of
great
significance
in
chemistry
and
has
been
intensively
investigated
the
last
few
decades.
From
perspective
green
chemistry,
oxygen
best
choice
as
terminal
oxidant
molecular
synthesis.
Hence,
aerobic
oxidative
functionalization
indoles
became
a
hot
research
topic
decade.
Numerous
efficient
protocols
this
field
have
discovered
that
enable
facile
transformations
to
related
valuable
compounds,
which
are
summarized
discussed
detail
review.
magnified
image
Green Synthesis and Catalysis,
Год журнала:
2021,
Номер
2(1), С. 78 - 81
Опубликована: Янв. 22, 2021
A
convenient
method
for
the
rapid
construction
of
indolo[2,3-b]indoles
has
been
developed.
This
cascade
reaction
involving
condensation,
dehydroaromatization,
and
oxidative
annulation
was
achieved
in
a
one-pot
TMSI/DMSO
system,
providing
diversity
functionalized
satisfactory
yields
under
facile
metal-free
conditions.
The
present
protocol
provides
straightforward
approach
to
access
structurally
valuable
indolo[2,3-b],
indoles.
Organic & Biomolecular Chemistry,
Год журнала:
2021,
Номер
19(29), С. 6380 - 6391
Опубликована: Янв. 1, 2021
Cyclohexanone
is
a
simple
and
widely
available
raw
material
that
can
be
obtained
from
lignin
biomass,
highlighting
its
renewable
sustainable
features.
Cyclohexanone,
as
an
important
synthon
in
organic
chemistry,
has
been
demonstrated
to
viable
for
constructing
functionalized
arenes
benzoheteroarenes,
with
recent
extensive
development
on
transition
metal-free
oxidative
dehydrogenative
aromatization.
This
review
focuses
research
progress
the
derivation
of
cyclohexanones
via
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(5), С. 3202 - 3210
Опубликована: Фев. 8, 2024
We
report
a
method
for
using
elemental
sulfur
to
facilitate
the
cyclization
of
aryl
hydrazones
and
isothiocyanates,
affording
biorelated
2-imino-1,3,4-thiadiazoles.
Reactions
progressed
in
presence
sulfur,
N-methylmorpholine
base,
DMSO
solvent,
while
were
tolerant
wide
range
functionalities
including
halogen,
nitro,
cyano,
methylsulfonyl,
heterocyclic
groups.
The
appears
offer
general
pathway
simple,
cheap,
stable
reagents
afford
triaryl-substituted
2-imino-1,3,4-thiadiazoles
under
relatively
mild
conditions.
