Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(34), P. 6407 - 6412
Published: Aug. 21, 2023
In
this
study,
we
developed
a
strategy
using
commercially
available
alkyl
iodides
and
O-benzoyl
oxime
to
efficiently
introduce
iminyl
groups
via
energy
transfer
halogen-atom
processes.
We
performed
three-component
1,2-carboimination
of
olefins
four-component
1,4-carboimination
across
alkynes,
resulting
in
the
synthesis
over
60
nitrogen-containing
molecules.
Moreover,
transformation
enables
molecules
with
sensitive
that
were
previously
difficult
achieve.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 12, 2024
The
ligated
boryl
radical
(LBR)
has
emerged
as
a
potent
tool
for
activating
alkyl
halides
in
transformations
through
halogen-atom
transfer
(XAT).
However,
unactivated
chlorides
still
present
an
open
challenge
this
strategy.
We
herein
describe
new
activation
mode
of
the
LBR
to
construct
C(sp
Chemical Science,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
The
Sonogashira-like
alkynylation
of
alkyl
halides
is
achieved
by
a
photocatalytic
approach
exploiting
amine-ligated
boryl
radicals
as
halogen-atom
transfer
mediators
in
combination
with
alkynyl
sulfones
SOMOphilic
reagents.
Synthesis,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 2, 2025
Abstract
Compounds
bearing
mono-
and
dibromomethyl
groups
are
extensively
utilized
in
synthetic
medicinal
chemistry.
In
this
regard,
selective
debromination
of
readily
or
easily
accessible
tribromomethyl
compounds
offers
a
direct
efficient
method
to
access
those
two
moieties.
work,
we
introduced
Lewis
base–borane-mediated
hydrodebromination
via
ionic
radical
pathway.
Using
4-(dimethylamino)pyridine–borane
(DMAP-BH3)
as
hydride
donor,
monohydrodebromination
was
achieved
nucleophilic
substitution
by
hydride,
delivering
groups.
On
the
other
hand,
treatment
with
an
N-heterocyclic
carbene–borane
(NHC-BH2CN)
boryl
precursor
presence
dilauroyl
peroxide
(DLP)
initiator
afforded
monobromomethyl
through
consecutive
bromine
atom
abstractions
cleave
C–Br
bonds.
Various
group
acetamides
acetates
were
applied
developed
protocol,
showcasing
good
functional
tolerance
broad
substrate
scope.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 17, 2025
This
paper
presents
a
novel
NHC-BH3-promoted
one-step
synthesis
of
disulfides
and
stibine
sulfides
using
odorless
sulfonyl
hydrazides.
The
protocol
tolerates
various
functional
groups
as
well
heterocyclic
compounds.
Mechanistic
studies
show
that
NHC-BH3
plays
two
roles:
(1)
reducing
hydrazides
into
(2)
promoting
the
cross-coupling
chlorostibine
with
disulfides.
synthesized
also
exhibit
satisfactory
anticancer
activity
against
4T1
MDA-MB-231
cancerous
cells.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(34), P. 6407 - 6412
Published: Aug. 21, 2023
In
this
study,
we
developed
a
strategy
using
commercially
available
alkyl
iodides
and
O-benzoyl
oxime
to
efficiently
introduce
iminyl
groups
via
energy
transfer
halogen-atom
processes.
We
performed
three-component
1,2-carboimination
of
olefins
four-component
1,4-carboimination
across
alkynes,
resulting
in
the
synthesis
over
60
nitrogen-containing
molecules.
Moreover,
transformation
enables
molecules
with
sensitive
that
were
previously
difficult
achieve.
