The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(17), С. 12583 - 12590
Опубликована: Авг. 19, 2024
A
protocol
induced
by
visible
light
for
the
direct
insertion
of
α-carbonyl
carbenes
into
B–H
bond
amine-borane
adducts
has
been
developed
under
conditions
that
are
free
metal
and
photocatalyst.
This
approach
provides
a
straightforward
route
to
various
organoboron
compounds
from
diazo
with
moderate
good
yields.
Mechanistic
investigations
reveal
this
photoinduced
reaction
proceeds
through
concerted
carbene
bond,
generation
α-diazo
esters
may
be
rate-determining
step.
ACS Catalysis,
Год журнала:
2022,
Номер
12(18), С. 11129 - 11136
Опубликована: Авг. 30, 2022
Herein,
we
report
visible
light
and
N-heterocyclic
carbene
(NHC)
jointly
promoted
multicomponent
transfer
reactions.
Under
the
optimized
reaction
conditions,
two
kinds
of
important
hydroxamic
acid
esters
were
obtained
in
good
yields
depending
on
media
used.
The
key
to
this
success
was
driven
by
blue
light-promoted
generation
free
species
fast
situ
formation
under
NHC-catalyzed
conditions.
mild
excellent
functional
group
tolerance,
useful
synthetic
transformations,
successful
modification
natural
products
drug
molecules
proved
utility
practicality
method.
Abstract
Vinyldiazo
compounds
are
one
of
the
most
important
synthons
in
construction
a
cyclic
ring.
Most
photochemical
transformations
vinyldiazo
mainly
focusing
on
utilization
their
C═C
bond
site,
while
reactions
taking
place
at
terminal
nitrogen
atom
largely
unexplored.
Herein,
photocatalytic
cascade
radical
cyclization
LBRs
with
reagents
through
sequential
B─N/C─N
formation
is
described.
The
reaction
starts
addition
(Lewis
base–boryl
radicals)
diazo
followed
by
intramolecular
to
access
wide
range
boron‐handled
pyrazoles
good
excellent
yields.
Control
experiments,
together
detailed
mechanism
studies
well
explain
observed
reactivity.
Further
demonstrate
utility
this
approach
for
applications
pharmaceutical
and
agrochemical
research.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(40)
Опубликована: Июль 28, 2023
The
control
of
the
reactivity
diazo
compounds
is
commonly
achieved
by
choice
a
suitable
catalyst,
e.g.
via
stabilization
singlet
carbenes
or
radical
intermediates.
Herein,
we
report
on
light-promoted
cyclic
imides
with
thiols,
where
solvent
results
in
two
fundamentally
different
reaction
pathways.
In
dichloromethane
(DCM),
carbene
formed
initially
and
engages
cascade
C-H
functionalization/thiolation
to
deliver
indane-fused
pyrrolidines
good
excellent
yields.
When
switching
acetonitrile
solvent,
pathway
shut
down
an
unusual
reduction
compound
occurs
under
otherwise
identical
conditions,
aryl
thiol
acts
as
reductant.
A
combined
set
experimental
computational
studies
was
carried
out
obtain
mechanistic
understanding
support
that
indane
formation
proceeds
insertion
triplet
carbene,
while
electron
transfer
process.
Organic Letters,
Год журнала:
2022,
Номер
24(36), С. 6647 - 6652
Опубликована: Сен. 2, 2022
A
visible-light-promoted
three
component
reaction
of
diazo
compounds,
nitriles,
and
carboxylic
acids
is
reported.
The
utilizes
acceptor-only
compounds
as
carbene
precursors
nitriles
carbene-trapping
reagents
to
form
the
key
nitrile
ylides.
Under
optimal
conditions,
a
wide
range
imide
products
were
obtained
in
good
excellent
yields.
gram-scale
synthesis
synthetic
application
isoquinoline-1,3(2H,4H)-dione
derivatives
further
proved
value
this
method.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 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.
Green Synthesis and Catalysis,
Год журнала:
2024,
Номер
5(3), С. 191 - 194
Опубликована: Авг. 1, 2024
A
copper-catalyzed
three-component
reaction
of
diazo
compounds,
nitriles,
and
azodicarboxylates
to
construct
2,3-dihydro-1,2,4-triazoles
is
reported.
Key
the
success
utilization
trap
in-situ
formed
nitrile
ylides
from
compounds
by
[3
+
2]-cycloaddition.
Both
acceptor-only
donor-acceptor
are
all
tolerated
strategy.
The
synthetic
value
this
protocol
illustrated
gram-scale
synthesis
valuable
transformation
obtained
2,3-dihydro-1,2,4-triazoles.
