Abstract
A
molecular
iodine‐catalyzed
system
for
the
coupling
reaction
of
4‐hydroxycoumarins
with
N
‐benzylic
sulfonamides
via
sp
3
C−N
bond
cleavage
has
been
established.
This
procedure
provides
a
series
C3‐alkylated
containing
structurally
diverse
functional
groups
in
good
to
excellent
yields.
Furthermore,
practicability
this
method
could
be
manifested
efficiently
gram‐scale
synthesis
drug
coumatetralyl
and
access
bioactive
agent
pyranocoumarin
from
obtained
product.
Chemical Reviews,
Год журнала:
2022,
Номер
122(15), С. 12544 - 12747
Опубликована: Июль 17, 2022
1,1,1,3,3,3-Hexafluoroisopropanol
(HFIP)
is
a
polar,
strongly
hydrogen
bond-donating
solvent
that
has
found
numerous
uses
in
organic
synthesis
due
to
its
ability
stabilize
ionic
species,
transfer
protons,
and
engage
range
of
other
intermolecular
interactions.
The
use
this
exponentially
increased
the
past
decade
become
choice
some
areas,
such
as
C–H
functionalization
chemistry.
In
review,
following
brief
history
HFIP
an
overview
physical
properties,
literature
examples
reactions
using
or
additive
are
presented,
emphasizing
effect
each
reaction.
Chemical Society Reviews,
Год журнала:
2024,
Номер
53(9), С. 4607 - 4647
Опубликована: Янв. 1, 2024
This
review
collectively
discussed
the
utilisation
of
alcohols
in
various
organic
transformations
and
their
application
toward
intermediates
drugs,
drug
derivatives
natural
product-like
molecules.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(7), С. 4790 - 4798
Опубликована: Март 29, 2023
A
hexafluoroisopropanol
(HFIP)-promoted
hydroxydifluoromethylation
of
aniline,
indole,
and
pyrrole
derivatives
with
difluoroacetaldehyde
ethyl
hemiacetal
has
been
developed.
This
protocol
provides
a
facile
straightforward
approach
to
access
diverse
difluoromethylated
carbinols
in
good
excellent
yields
under
mild
conditions.
Furthermore,
gram-scale
synthetic
derivatization
experiments
have
also
demonstrated.
Organic Letters,
Год журнала:
2020,
Номер
23(2), С. 358 - 364
Опубликована: Дек. 23, 2020
The
switchable
synthesis
of
3-non,
3-mono,
3,3′-disubstituted
3,4-dihydroquinolin-2(1H)-ones
was
developed
through
a
redox-neutral
hydride-transfer/N-dealkylation/N-acylation
strategy
from
o-aminobenzaldehyde
with
4-hydroxycoumarin,
and
Meldrum's
acid,
respectively.
unprecedented
for
the
3,3′-highly
functionalized
3,4-dihydroquinolin-2(1H)-one
has
been
realized
in
situ
utilization
released
HCHO
via
o-QM
involved
Michael
addition.
In
addition,
synthetic
utility
this
protocol
well
illustrated
concise
CYP11B2
inhibitor.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(2), С. 1144 - 1153
Опубликована: Янв. 7, 2022
A
novel
efficient
HFIP-catalyzed
synthesis
of
structurally
diverse
2,2-difluoro-3-hydroxy-1,4-diketone
derivatives
from
readily
available
glyoxal
monohydrates
and
difluoroenoxysilanes
is
described.
This
convenient
protocol
induced
by
the
distinctive
fluorine
effect
reactants
fluoroalcohol
catalyst,
which
represents
first
application
catalysis
in
a
Mukaiyama
aldol
reaction.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(3), С. 2050 - 2054
Опубликована: Янв. 19, 2024
The
first
total
synthesis
of
cadinane
sesquiterpenoid
alanense
A,
in
which
an
intramolecular
dehydrative
Friedel–Crafts
alkylation
2,5-diaryl-2-pentanol
is
incorporated
as
a
key
step,
has
been
achieved.
combinatorial
use
p-TsOH·H2O
catalyst
and
1,1,1,3,3,3-hexafluoro-2-propanol
(HFIP)
solvent
provides
1,1-disubstituted
tetrahydronaphthalene
97%
yield.
It
was
also
found
that
the
combination
p-TsOH
HFIP
effective
for
removal
phenolic
MOM
ether.
Synthesis,
Год журнала:
2024,
Номер
56(11), С. 1756 - 1764
Опубликована: Янв. 25, 2024
Abstract
A
facile
and
efficient
method
for
the
synthesis
of
trifluoromethylated
carbinols
has
been
developed
from
imidazo[1,2-a]pyridines
trifluoroacetaldehyde.
The
direct
C(sp2)–H
hydroxytrifluoromethylation
is
successfully
implemented
at
room
temperature
using
HFIP
as
solvent
through
dehydrative
cross-coupling
process,
which
displays
a
broad
substrate
scope
functional
group
tolerance.
Furthermore,
gram-scale
synthetic
transformation
experiments
have
also
demonstrated,
indicate
its
potential
applicable
values
in
organic
synthesis.
This
green
protocol
features
operational
simplicity,
atom
economy,
mild
reaction
conditions
(e.g.,
temperature,
transition-metal-
oxidant-free,
without
inert
gas
protection),
wide
scope,
excellent
practicality.
ACS Omega,
Год журнала:
2025,
Номер
10(4), С. 4163 - 4169
Опубликована: Янв. 21, 2025
An
environmentally
friendly,
cheap,
and
scalable
protocol
for
direct
lawsone
O-alkylation
employing
different
alcohols
using
acid
chitosan
(CS–SO3H)
as
a
heterogeneous
organocatalyst
is
described
herein
the
first
time.
A
wide
variety
of
can
be
converted
with
functional
group
tolerance
high
atomic
economy.
Significantly,
catalyst
recycling
method
chemoselectivity
were
also
assessed.
