Angewandte Chemie,
Год журнала:
2024,
Номер
136(45)
Опубликована: Июль 17, 2024
Abstract
1,2‐Diamination
of
alkenes
represents
an
attractive
way
to
generate
differentiated
vicinal
diamines,
which
are
prevalent
motifs
in
biologically
active
compounds
and
catalysts.
However,
existing
methods
usually
limited
scope
produce
diamines
where
one
or
both
nitrogens
protected,
adding
synthetic
steps
for
deprotection
further
N‐functionalization
reach
a
desired
target.
Furthermore,
the
range
amino
groups
that
can
be
introduced
at
internal
position
is
fairly
limited.
Here
we
describe
1,2‐diamination
styrenes
directly
installs
free
group
terminal
wide
variety
unprotected
nitrogen
nucleophiles
(primary
secondary
alkyl
aromatic
amines,
sulfoximines,
N
‐heterocycles,
ammonia
surrogate)
position.
Two
complementary
sets
conditions
encompass
electronically
activated
deactivated
with
diverse
substitution
patterns
functional
groups.
Moreover,
this
strategy
extended
1,2‐aminothiolation
styrenes.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Июнь 2, 2025
A
facile
base-mediated
cyclization
and
rearrangement
of
enamine
thianthrenium
salts
for
the
construction
indole
compounds
is
disclosed.
In
this
reaction,
sequential
cleavage
two
C-S
bonds
subsequent
formation
C-N
C-C
furnish
a
series
substituted
indoles
in
moderate
to
good
yields.
Furthermore,
an
efficient
late-stage
functionalization
established.
The
method
features
wide
substrate
scope,
functional
group
tolerance,
low-cost
starting
materials.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(7), С. 4319 - 4325
Опубликована: Март 23, 2024
Earth-abundant-metal
catalyzed
double
bond
transposition
offers
a
sustainable
and
atom-economical
route
toward
the
synthesis
of
internal
alkenes.
With
an
emphasis
specifically
on
olefins
ethers,
isomerization
allylic
amines
has
been
particularly
under
represented
in
literature.
Herein,
we
report
efficient
methodology
for
selective
N-allylic
organic
compounds,
including
amines,
amides,
imines.
The
reaction
is
by
neutral
PCNHCP
cobalt(I)
pincer
complex
proceeds
via
π-allyl
mechanism.
occurs
readily
at
80–90
°C,
it
compatible
with
wide
variety
functional
groups.
situ
formed
enamines
could
additionally
be
used
one-pot
inverse-electron-demand
Diels–Alder
to
furnish
series
diversely
substituted
heterobiaryls,
which
further
discussed
this
report.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(45)
Опубликована: Июль 17, 2024
1,2-Diamination
of
alkenes
represents
an
attractive
way
to
generate
differentiated
vicinal
diamines,
which
are
prevalent
motifs
in
biologically
active
compounds
and
catalysts.
However,
existing
methods
usually
limited
scope
produce
diamines
where
one
or
both
nitrogens
protected,
adding
synthetic
steps
for
deprotection
further
N-functionalization
reach
a
desired
target.
Furthermore,
the
range
amino
groups
that
can
be
introduced
at
internal
position
is
fairly
limited.
Here
we
describe
1,2-diamination
styrenes
directly
installs
free
group
terminal
wide
variety
unprotected
nitrogen
nucleophiles
(primary
secondary
alkyl
aromatic
amines,
sulfoximines,
N-heterocycles,
ammonia
surrogate)
position.
Two
complementary
sets
conditions
encompass
electronically
activated
deactivated
with
diverse
substitution
patterns
functional
groups.
Moreover,
this
strategy
extended
1,2-aminothiolation
styrenes.
Chem Catalysis,
Год журнала:
2023,
Номер
3(12), С. 100813 - 100813
Опубликована: Ноя. 14, 2023
Enamides
are
versatile
building
blocks
in
organic
synthesis
that
give
access
to
complex
nitrogen-containing
compounds.
However,
despite
the
interest
these
compounds,
synthetic
strategies
enamides
with
carbon-centered
chirality
atre
scarce.
In
this
work,
we
report
an
efficient
method
for
of
a
new
class
chiral
trifluoromethylated
stereogenic
center
from
easily
accessible
allylic
amines
by
effective
chirality-transfer
process.
The
gives
excellent
yields
and
diastereo-
enantioselectivities.
scope
reaction
is
broad,
various
substituents
functional
groups
tolerated.
Furthermore,
transformations
were
carried
out
trifluoromethylated,
structures.
For
example,
photocatalytic
E/Z
isomerization
also
presented.
Chemical and Pharmaceutical Bulletin,
Год журнала:
2024,
Номер
72(5), С. 432 - 453
Опубликована: Апрель 30, 2024
We
have
developed
efficient
synthetic
reactions
using
enamines
and
enamides
carrying
oxygen
atom
substituent
on
nitrogen,
such
as
N-alkoxyenamines,
N,α-dialkoxyenamines,
N-alkoxyanamides,
N-(benzoyloxy)enamides.
The
umpolung
reaction
by
polarity
inversion
at
the
β-position
of
N-alkoxyenamines
afforded
α-alkyl-,
α-aryl-,
α-alkenyl-,
α-heteroarylketones
aluminum
reagent
nucleophiles.
Furthermore,
one-pot
α-phenylation
ketones
has
been
also
developed.
applied
this
method
to
N,α-dialkoxyenamine,
generated
from
N-alkoxyamide
afford
α-arylamides.
vicinal
functionalization
achieved
with
formation
two
new
carbon–carbon
bonds
an
organo-aluminum
subsequent
allyl
magnesium
bromide
or
tributyltin
cyanide.
A
sequential
retro-ene
arylation
for
conversion
N-alkoxyenamides
corresponding
tert-alkylamines.
[3,3]-sigmatropic
rearrangement
N-(benzoyloxy)enamides
followed
cyclic
β-aryl-β-amino
alcohols
bearing
a
tetrasubstituted
carbon
center.
resulting
products
were
converted
into
sterically
congested
β-amino
alcohols,
well
dissociative
anesthetic
agent
Tiletamine.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(14), С. 10014 - 10019
Опубликована: Июль 7, 2023
The
Spin-Center
Shift
(SCS)
elimination
is
a
specific
way
for
the
generation
of
radicals
with
relevance
in
synthetic
and
biochemical
pathways.
combination
SCS-mediated
radical
chemistry
atom-transfer
addition
(ATRA)
offers
new
directions
diversity-oriented
chemical
synthesis.
Herein,
we
report
photoredox
three-component
reaction
α-acyloxy-N-heterocycles
as
precursors,
styrene
derivatives
trapping
agents,
alcohols
nucleophilic
quenchers.
novel
radical-polar
crossover
provides
access
to
diverse
set
branched
ethers
possessing
high
structural
complexity.
utility
transformation
was
also
demonstrated
by
synthesis
complex
drug
derivative
it
easily
scalable
multigram
level.
scope
limitations
were
explored
plausible
mechanism
proposed.
Catalysts,
Год журнала:
2023,
Номер
13(6), С. 919 - 919
Опубликована: Май 23, 2023
A
new
and
powerful
visible-light-induced
difunctionalization
of
the
C-C
σ-bond
alkylidenecyclopropanes
via
a
ring-opening
process
was
developed.
Importantly,
acyl
chlorides
are
used
as
both
Cl
sources.
This
strategy
provides
an
effective
route
for
bond
with
radical
Cl−
to
construct
C-Cl
in
one
pot.
In
addition,
it
has
wide
range
substrates
can
tolerate
various
functional
groups.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(20), С. 14487 - 14493
Опубликована: Сен. 28, 2023
Methyl
substitution
at
the
double
bond
of
N-alkenyl
anilides
influences
both
preferred
conformation
and
susceptibility
to
acidic
hydrolysis.
The
R1-substituted
amide
favors
trans
conformation,
whereas
amides
substituted
R2
or
R3
favor
cis
conformation.
Substitution
R1
positions
increases
ratio
conformer.
DFT
study
indicated
that
these
conformational
preferences
can
be
explained
in
terms
substituent-induced
torsion
twisting
moiety
relative
plane.
enhances
hydrolysis,
stability.
effect
on
was
showcased
by
contrasting
anilide
(trans)
hydrogenated
N-isopropyl
(cis).
New Journal of Chemistry,
Год журнала:
2024,
Номер
48(28), С. 12793 - 12799
Опубликована: Янв. 1, 2024
An
I
2
-mediated
β-C(sp
)–H
chalcogenylation
of
enamides
under
mild
and
rapid
conditions
has
been
developed.
Sequential
addition
PIFA
led
to
valuable
5-thio-
5-seleno-2-pyridones
with
a
free
C3
position.
