Organic Letters,
Год журнала:
2023,
Номер
25(48), С. 8716 - 8721
Опубликована: Ноя. 22, 2023
2-Azidoimines
are
versatile
precursors
to
value-added
vicinal
unsymmetrical
diamines,
which
among
the
most
common
motifs
in
biologically
active
compounds.
Herein,
we
report
their
operationally
simple
synthesis
through
a
highly
regioselective
intermolecular
azidoamination
of
olefins
under
metal-free
conditions.
The
approach
proceeded
azide
and
iminyl,
two
differentiated
N-centered
radicals.
synthetic
potential
protocols
was
further
established
via
condensation/amination
sequential
cascade
chemoselective,
orthogonal
transformations
access
primary
diamines.
Organic Letters,
Год журнала:
2024,
Номер
26(40), С. 8447 - 8452
Опубликована: Авг. 22, 2024
Owing
to
their
diverse
biological
activities
and
versatility
as
synthetic
precursors,
organoselonocyanes
categorize
themselves
vital
compounds.
However,
a
limited
reagent
pool
restricts
utility.
In
the
present
work,
alkyl
selenocyanates
are
hereby
established
new
bifunctional
reagents
for
simultaneous
transfer
of
an
group
in
addition
−SeCN.
These
reagents,
when
merged
with
photocatalysis,
provide
key
accessing
organoselenocyanates
from
feedstock
olefins
efficient
atom-economic
fashion.
A
route
analogous
isoselenocyanate
isomers
facilitated
by
Lewis
acid
catalysis
is
also
reported,
presenting
divergent
strategy
both
ambident
−SeCN
manner.
Organic Letters,
Год журнала:
2023,
Номер
25(50), С. 9047 - 9052
Опубликована: Дек. 12, 2023
Activated
by
visible
light,
arylazo
sulfones
can
serve
as
multifaceted
reactants
and
are
employed
in
diazenylation,
sulfonylation,
arylation
reactions
under
(photo)catalyst-free
conditions.
Such
versatile
reactivity
enabled
us
to
develop
an
operationally
simple,
regioselective,
tunable
difunctionalization
of
styrenes
with
produce
α-sulfonyl
arylhydrazones
1,2-alkoxyarylated
products
moderate
excellent
yields.
Furthermore,
such
difunctionalized
have
been
exploited
key
building
blocks
for
the
synthesis
various
heterocycles.
Green Synthesis and Catalysis,
Год журнала:
2024,
Номер
unknown
Опубликована: Авг. 1, 2024
A
highly
selective
and
atom-economical
multi-component
remote
difunctionalization
strategy
has
been
successfully
developed.
This
utilizes
precise
control
over
the
radical
properties
of
bifunctional
precursors
electronic
traits
olefins
diazenes
to
achieve
effective
radical-mediated
1,4-oxyimination/diamination
across
C=C
N=N
bonds.
By
capitalizing
on
compatibility
reactivity
tuning,
this
approach
enables
synthesis
complex
triazine
compounds
with
an
N-N-N
framework,
providing
a
versatile
tool
for
constructing
diverse
molecular
structures.
metal-free
method
is
atom-efficient
adaptable
various
substrates,
demonstrating
remarkable
tolerance
broad
range
functional
groups.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
89(1), С. 656 - 664
Опубликована: Дек. 7, 2023
We
demonstrate
that
oxime
ester
derivatives
can
be
used
as
both
a
halogen
atom
transfer
(XAT)
agent
and
an
imine
source
under
photocatalytic
conditions,
allowing
the
radical
amination
of
alkyl
halides,
resulting
in
formation
broad
scope
imines.
Hydrolysis
latter
gives
direct
access
to
corresponding
primary
amines.
Mechanistically,
reaction
is
believed
proceed
through
aryl
intermediates,
which
are
responsible
for
activation
halides
via
XAT.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(44)
Опубликована: Сен. 1, 2023
Utilization
of
oxime
ethers
as
bifunctional
reagents
remains
unknown.
Herein,
we
present
a
mechanistically
distinct
strategy
that
enables
oximesulfonylation
olefins
using
sulfonyl-oxime-ethers
under
metal-free
photochemical
conditions.
Via
concomitant
C-S
and
C-C
bond
formation,
the
process
permits
incorporation
sulfonyl
groups
into
in
complete
atom-economic
fashion,
providing
rapid
access
to
multi-functionalized
β-sulfonyl
with
good
yields
stereoselectivity.
The
method
is
amenable
functionalization
complex
bioactive
molecules
shown
be
scalable.
A
radical
chain
mechanism
initiated
via
Hydrogen
Atom
Transfer
(HAT)
mediated
N-O
cleavage
suggested
for
process,
based
on
our
results
mechanistic
investigations.
Green Chemistry,
Год журнала:
2024,
Номер
26(9), С. 5471 - 5476
Опубликована: Янв. 1, 2024
The
photocatalytic
α-aminoalkyl
radical
addition
of
amines
faciliated
by
benzophenone
is
disclosed.
This
an
example
a
alkylation
method
that
uses
low-toxicity
solvents
and
mild
reaction
conditions.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(16), С. 3430 - 3437
Опубликована: Апрель 10, 2024
Abstract
In
this
manuscript
a
general
photocatalytic
approach
for
the
synthesis
of
alkyl‐substituted
gem
‐difluoroalkenes
using
readily
available
oxime
esters
and
1‐bromo‐1,1‐difluoroprop‐2‐ene
(BDFP)
has
been
established.
This
strategy
involving
radical
bromo
elimination
provides
access
to
large
variety
value‐added
fluorinated
molecules.
The
mild
reaction
conditions
are
compatible
with
many
functional
groups
including
complex
natural
products
or
drug
Experimental
theoretical
mechanistic
investigations
indicate
that
efficiency
process
relies
on
crucial
role
imine
radical,
which
is
formed
after
photoexcitation
via
energy
transfert
(EnT)
decarboxylation
ester.
Indeed,
would
either
behave
as
bromine
scavenger
an
XAT
promoter
in
reaction.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(23), С. 4641 - 4646
Опубликована: Янв. 1, 2024
A
novel
two-step
synthesis
of
β-trifluoromethyl
primary
amines
from
readily
available
α-(trifluoromethyl)styrenes
and
phthalimide
is
developed.
The
first
step
involves
a
hydroamination
between
(PhthNH)
with
the
assistance
base.
Next,
hydrazinolysis
resulting
