Organic Letters,
Год журнала:
2021,
Номер
23(16), С. 6429 - 6434
Опубликована: Авг. 4, 2021
In
the
course
of
upscaling
synthesis
enantiopure
aryliodine
precatalysts,
we
detected
an
unreported
meso
form
catalysts
for
first
time.
A
new
scalable
route
was
developed
to
avoid
epimerization
lactamide
arms,
providing
syntheses
precatalysts
that
are
both
more
effective
and
much
less
time-consuming.
The
obtained
with
these
synthetic
procedures
have
been
employed
in
some
published
reactions,
reaching
maximum
ee
ever
reported.
Chemical Society Reviews,
Год журнала:
2022,
Номер
51(18), С. 8102 - 8139
Опубликована: Янв. 1, 2022
Hypervalent
iodine
compounds
as
environmentally
friendly
and
relatively
inexpensive
reagents
have
properties
similar
to
transition
metals.
They
are
employed
alternatives
metal
catalysts
in
organic
synthesis
mild,
nontoxic,
selective
recyclable
catalytic
reagents.
Formation
of
C-N,
C-O,
C-S,
C-F
C-C
bonds
can
be
seamlessly
accomplished
by
hypervalent
catalysed
oxidative
functionalisations.
The
aim
this
review
is
highlight
recent
developments
the
utilisation
iodine(III)
iodine(V)
a
wide
range
including
chiral
for
stereoselective
synthesis.
Polymer-,
magnetic
nanoparticle-
framework-supported
also
described.
Journal of the American Chemical Society,
Год журнала:
2022,
Номер
144(4), С. 1962 - 1970
Опубликована: Янв. 19, 2022
N-CF3
compounds
constitute
valuable
targets
in
medicinal
chemistry.
Extensive
studies
have
been
reported
for
the
preparation
of
through
fluorination
and
trifluoromethylation
N-containing
compounds.
The
development
new
synthetic
methods
from
abundant
easily
available
substrates
is
highly
desirable
but
still
challenging.
Herein,
we
report
design
synthesis
novel
N-Cbz-
N-Boc-N-trifluoromethyl
hydroxylamine
reagents
by
silver-mediated
oxidative
trifluoromethylation.
These
successfully
applied
to
direct
incorporation
a
NCF3
moiety
into
commonly
used
unsaturated
under
photoredox
catalysis.
This
protocol
enables
efficient
regioselective
C-H
trifluoromethylamination
various
(hetero)arenes,
including
complex
bioactive
molecules.
Furthermore,
variety
alkenes,
dienes,
isonitriles
undergo
tandem
trifluoromethylamination/functionalization
delivering
structurally
diverse
N-trifluoromethyl
aliphatic
heteroaromatic
amines.
Notably,
previously
unknown
cyclic
oxazolidinones
oxazolones
were
conveniently
prepared
with
reagents.
diversification
resulting
α-trifluoromethylamino
ketones
afforded
largely
underexplored
N-alkenyl-
N-alkynyl-N-CF3
Journal of the American Chemical Society,
Год журнала:
2022,
Номер
144(41), С. 18803 - 18809
Опубликована: Окт. 4, 2022
A
method
for
the
regiodivergent
aminooxygenation
of
aryl
olefins
under
electrophotocatalytic
conditions
is
described.
The
procedure
employs
a
trisaminocyclopropenium
(TAC)
ion
catalyst
with
visible
light
irradiation
controlled
electrochemical
potential
to
convert
corresponding
oxazolines
high
chemo-
and
diastereoselectivity.
With
judicious
choice
between
two
inexpensive
abundant
reagents,
namely
water
urethane,
either
2-amino-1-ol
or
1-amino-2-ol
derivatives
could
be
prepared
from
same
substrate.
This
amenable
multigram
synthesis
oxazoline
products
low
loadings.
Journal of the American Chemical Society,
Год журнала:
2023,
Номер
145(15), С. 8299 - 8307
Опубликована: Апрель 6, 2023
Modular
strategies
to
rapidly
increase
molecular
complexity
have
proven
immensely
synthetically
valuable.
In
principle,
transformation
of
an
alkene
into
a
dielectrophile
presents
opportunity
deliver
two
unique
nucleophiles
across
alkene.
Unfortunately,
the
selectivity
profiles
known
dielectrophiles
largely
precluded
this
deceptively
simple
synthetic
approach.
Herein,
we
demonstrate
that
dicationic
adducts
generated
through
electrolysis
alkenes
and
thianthrene
possess
profile
relative
more
conventional
dielectrophiles.
Specifically,
these
species
undergo
single
perfectly
regioselective
substitution
reaction
with
phthalimide
salts.
This
observation
unlocks
appealing
new
platform
for
aminofunctionalization
reactions.
As
illustrative
example,
implement
reactivity
paradigm
address
longstanding
challenge:
diamination
distinct
nitrogen
nucleophiles.
Studies
mechanism
process
reveal
key
alkenyl
thianthrenium
salt
intermediate
controls
exquisite
regioselectivity
highlight
importance
proton
sources
in
controlling
sulfonium
electrophiles.
Journal of the American Chemical Society,
Год журнала:
2021,
Номер
143(33), С. 13408 - 13417
Опубликована: Авг. 10, 2021
The
chemo-,
regio-,
diastereo-,
and
enantioselective
1,2-oxyamination
of
alkenes
using
selenium(II/IV)
catalysis
with
a
chiral
diselenide
catalyst
is
reported.
This
method
uses
N-tosylamides
to
generate
oxazoline
products
that
are
useful
both
as
protected
1,2-amino
alcohol
motifs
ligands.
reaction
proceeds
in
good
yields
excellent
enantio-
diastereoselectivity
for
variety
pendant
functional
groups
such
sulfonamides,
alkyl
halides,
glycol-protected
ketones.
Furthermore,
the
rapid
generation
demonstrated
expeditious
assembly
PHOX
ligands
well
diversely
amino
alcohols.
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(23), С. 5168 - 5195
Опубликована: Окт. 20, 2021
Abstract
Oxazolidinone
represents
a
class
of
most
important
five‐membered
cyclic
carbamates.
They
are
great
significance
for
modern
organic
synthesis
and
widespread
as
pharmacologically
active
compounds.
This
review
summarizes
recent
advances
in
the
chemistry
2‐oxazolidinones,
with
an
emphasis
on
their
synthesis,
employing
different
catalytic
systems
or
catalyst‐free
conditions,
well
ring‐opening
transformations
through
decarboxylative
coupling,
covering
period
from
2010
to
early
2021.
Detailed
mechanistic
aspects
highlighted,
hoping
help
researchers
explore
hidden
opportunities
reaction
discoveries.
magnified
image
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(23), С. 3974 - 4005
Опубликована: Окт. 20, 2022
Abstract
Halogen
(fluorine,
chlorine,
bromine,
iodine)
or
chalcogen
(sulfur,
selenium)‐containing
heterocycles
are
widely
recognized
as
key
building
blocks
in
many
natural
products
and
bioactive
targets.
Catalytic
asymmetric
halogenation/chalcogenation
of
carbon‐carbon
unsaturated
bonds
via
onium
ion
transformations
efficient
methods
to
obtain
diverse
chiral
heterocyclic
backbones.
In
the
past
few
years,
catalytic
enantioselective
versions
halo/thio/seleno‐functionalizations
with
various
halogen
electrophiles
have
experienced
constant
development.
This
review
highlights
those
advances
preparing
functionalized
promoted
by
organocatalysts
metal‐based
catalysts.
magnified
image
Green Chemistry,
Год журнала:
2023,
Номер
25(3), С. 978 - 985
Опубликована: Янв. 1, 2023
The
telescoped
electrochemical
coupling
of
NH
3
and
CO
2
with
simple
aromatic
olefins
is
described,
forming
valuable
N-heterocycles
in
an
atom-efficient
manner
overall
yields
up
to
91%.
same
iodide
catalyst
required
for
both
steps.
JACS Au,
Год журнала:
2021,
Номер
1(6), С. 734 - 741
Опубликована: Апрель 29, 2021
A
novel
iodide-catalyzed
intermolecular
aminooxygenation
strategy
is
described
here.
Amide
used
as
the
O-
and
N-
source
to
probe
for
regiocontrol
strategies.
Notably,
simple
additives
can
be
selectively
introduced
achieve
regiodivergent
oxyamination
processes
electronically
activated
alkenes
while
being
regio-complementary
unactivated
alkenes.
Our
preliminary
data
demonstrates
that
this
based
on
nucleophile
also
applied
in
asymmetric
using
chiral
hypervalent
iodine
catalysis.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(20), С. 4163 - 4180
Опубликована: Янв. 1, 2023
A
number
of
organic
transformations
have
been
achieved
using
hypervalent
iodine
reagents
under
mild
reaction
conditions.
The
use
these
as
chiral
organocatalyst
exhibited
highly
selective
asymmetric
reactions.
