Synlett,
Год журнала:
2022,
Номер
33(19), С. 1917 - 1924
Опубликована: Авг. 25, 2022
Abstract
A
novel
method
for
assembling
pyrrolidine-2,4-diones
from
1,5-enenitriles
and
acetone/acetonitrile
via
a
cyclization/hydrolysis
has
been
established
under
metal-catalyst-
base-free
conditions,
with
Oxone
as
green
oxidant
H2O
an
additive
at
90–110
℃.
This
strategy
is
highlighted
by
of
alkyl
cyanides,
achieving
direct
C(sp3)–H
oxidative
functionalization,
giving
full
conversion
the
substrates
excellent
functional
group
compatibility.
Chemical Communications,
Год журнала:
2022,
Номер
58(75), С. 10442 - 10468
Опубликована: Янв. 1, 2022
Fluorine
compounds
are
known
for
their
abundance
in
more
than
20%
of
pharmaceutical
and
agrochemical
products
mainly
due
to
the
enhanced
lipophilicity,
metabolic
stability
pharmacokinetic
properties
organofluorides.
Consequently,
last
decade
has
seen
enormous
growth
incorporation
a
trifluoromethyl
group
into
organic
motifs.
With
significance,
this
review
aims
provide
complete
picture
transition
metal-mediated
construction
C(sp3,
sp2,
sp)-CF3
bonds
via
C-H/X
bond
functionalization
or
addition
processes
both
aliphatic
aromatic
hydrocarbons.
Diversified
reagents
ranging
from
radical
electrophilic
nucleophilic
trifluoromethylating
agents
respective
mechanisms
have
been
further
deliberated
comprehensive
overview.
The
coverage
on
topic
is
expected
make
unique
beneficial
future
applications
enriching
community
towards
improvements
field
trifluoromethylation
reactions,
turn
improving
propensity
development
drugs.
Chemical Reviews,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 13, 2024
Hypervalent
iodine(III)
compounds
have
found
wide
application
in
modern
organic
chemistry
as
environmentally
friendly
reagents
and
catalysts.
iodine
are
commonly
used
synthetically
important
halogenations,
oxidations,
aminations,
heterocyclizations,
various
oxidative
functionalizations
of
substrates.
Iodonium
salts
arylating
reagents,
while
iodonium
ylides
imides
excellent
carbene
nitrene
precursors.
Various
derivatives
benziodoxoles,
such
azidobenziodoxoles,
trifluoromethylbenziodoxoles,
alkynylbenziodoxoles,
alkenylbenziodoxoles
group
transfer
the
presence
transition
metal
catalysts,
under
metal-free
conditions,
or
using
photocatalysts
photoirradiation
conditions.
Development
hypervalent
catalytic
systems
discovery
highly
enantioselective
reactions
chiral
represent
a
particularly
recent
achievement
field
chemistry.
Chemical
transformations
promoted
by
many
cases
unique
cannot
be
performed
any
other
common,
non-iodine-based
reagent.
This
review
covers
literature
published
mainly
last
7-8
years,
between
2016
2024.
A
Cu-catalyzed
relay
process
for
the
preparation
of
diazidated
quinazolinone
and
polycyclic
imidazole
derivatives
in
which
readily
available
alkene-tethered
substrates
undergo
an
addition/cyclization/C(sp3)–H
functionalization
alkene
sequences
with
high
efficiency
is
described.
Various
functionalized
N-heteropolycyclic
compounds
were
prepared
good
yields
a
broad
substrate
scope.
Moreover,
direct
azidation
α-C(sp3)–H
bond
corresponding
N-heterocycles
has
been
demonstrated
on
basis
mechanistic
studies,
provide
alternative
late-stage
approach
derivatization
N-heterocyclic
scaffolds.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(4), С. 2718 - 2725
Опубликована: Фев. 2, 2024
An
anodically
oxidizing
trifluoromethylation
cascade
of
N-cyanamide
alkene
bearing
two
electronically
differentiated
olefin
moieties
was
reported,
in
which
various
N-unsaturated
acyl
cyanamide
alkenes
and
CF3SO2Na
acting
as
readily
available
starting
materials
furnished
nonaromatic
fused
azaheterobicyclic
compounds
a
highly
efficient
sustainable
manner.
The
broad
substrate
scope,
facile
scalability,
sustainability
enabled
this
electrochemical
process
to
be
an
appealing
complement
for
trifluoromethylated
cyclic
amidines.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(33), С. 6715 - 6718
Опубликована: Янв. 1, 2023
Using
CF
3
SO
2
Na
as
the
radical
source,
an
eco-friendly
approach
for
electrochemistry-mediated
cascade
cyclization
of
N
-methacryloyl-2-phenylbenzoimidazoles
was
described.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(9), С. 5882 - 5892
Опубликована: Апрель 12, 2022
A
tandem
addition/cyclization
reaction
between
trifluoromethyl
N-acylhydrazones
and
cyanamide
is
described,
which
provides
a
novel
efficient
process
for
the
synthesis
of
polysubstituted
3-trifluoromethyl-1,2,4-triazolines
their
derivatives.
The
method
has
advantages
mild
conditions,
broad
substrate
scope,
good
product
yields,
atom
economy.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(21), С. 5912 - 5920
Опубликована: Янв. 1, 2022
An
electrochemical
trifluoromethylative
cyclization
of
N
-cyanamide
alkenes
and
alkynes
is
presented,
which
afforded
(bis)-C,
-trifluoromethylated
cyclic
amidines,
azines
amides
with
selective
multiple
bond
formations
in
a
controllable
manner.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(23), С. 16090 - 16098
Опубликована: Ноя. 12, 2022
We
report
herein
a
facile
strategy
to
synthesize
trifluoromethylated
γ-lactams
through
trifluoromethylcarbonylation
of
N-cyano
alkenes
using
readily
available
CF3SO2Na
as
the
CF3
radical
source.
A
range
trifluoromethyl-containing
was
obtained
in
good
yields.
This
transition-metal-free
protocol
is
demonstrated
with
mild
conditions,
broad
substrate
scope,
functional
group
tolerance,
convenient
reagents,
and
an
easy-to-handle
operating
system.
