The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(21), P. 15733 - 15738
Published: Oct. 16, 2024
Remarkable
progress
has
been
made
in
the
radical
cascade
cyclization
of
heteroaryl-
or
aryl-tethered
alkenes
to
construct
benzene-fused
frameworks
via
cracking
aryl
C–H
bonds.
In
contrast,
linear
dienes
through
vinyl
bonds
nonbenzene-fused
ring
with
endocyclic
double
significantly
lagged
behind,
and
major
advances
have
largely
restricted
generation
5-membered
heterocycles,
such
as
pyrrolinones.
Herein,
we
report
silver-mediated
regioselective
sulfonylation-cyclization
sodium
sulfinates
form
sulfonylated
6-
7-membered
cyclic
enamines.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(10), P. 2062 - 2067
Published: March 7, 2024
The
use
of
readily
available
and
diverse
sulfamoyl
chlorides
for
synthesizing
sulfonamide
compounds
presents
an
intriguing,
yet
significantly
underexplored
strategy.
Activating
via
single-electron
reduction
poses
challenges
due
to
their
high
potential.
Alternatively,
the
SO2–Cl
bond
in
could
be
cleaved
by
XAT.
However,
existing
methodologies
have
been
limited
either
photocatalyst
or
monofunctionalization
activated
alkenes.
Here,
we
report
a
regioselective
sulfamoyl-oximation
alkenes
involving
activation
through
HAT
XAT
relay
strategy
photocatalyst-free
way.
key
this
success
lies
dual
roles
tert-butyl
nitrite
(TBN),
which
not
only
serves
as
source
oximes
but
also
acts
reagent
generate
crucial
reactive
species.
exclusion
metal
catalysts
photosensitizers
utilizing
light
energy
renders
protocol
versatile
universally
applicable
broad
range
structurally
oxime-containing
alkyl
sulfonamides.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(9), P. 6513 - 6524
Published: April 13, 2024
Efficient
synthesis
of
sulfonamides
has
long
been
pursued
by
chemists
due
to
their
frequent
occurrence
in
pharmaceuticals,
especially
anti-inflammatory
medicines.
The
traditional
assembly
from
sulfonyl
chlorides
and
amines,
as
well
the
recently
developed
one-step
involving
sulfur
dioxide,
still
faces
challenges
such
poor
substrate
compatibility
and/or
stringent
reaction
conditions.
Herein,
we
present
a
strategy
for
situ
generation
sulfamoyl
radicals
modular
both
alkenyl
alkyl
with
wide
applicability
(>100
examples),
mild
conditions,
easily
accessible
starting
materials.
This
method
is
successfully
applied
late-stage
modification
drug
molecules
(23
molecule
naratriptan,
15N-labeling
sulfonamides.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(17), P. 3673 - 3678
Published: April 19, 2024
Herein,
rhodium(III)-catalyzed
β-C(sp2)–H
alkenylation
and
alkylation
of
enamides
are
presented
using
readily
accessible
allylic
alcohols
by
switching
the
reaction
conditions.
This
tunable
transformation
has
been
applied
to
a
wide
range
substrates
typically
proceeded
with
excellent
regioselectivity
stereoselectivity
as
well
good
functional
group
tolerance.
The
catalytic
system
offers
an
efficient
approach
for
synthesizing
various
functionalized
bearing
N-(2Z,4E)-butadiene
(Z)-β-C(sp2)–H
alkylated
enamides.
In
addition,
mechanistic
experiments
suggest
that
Rh(III)-catalyzed
C–H
activation
is
not
related
critical
step.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 1, 2025
In
this
study,
we
have
devised
a
strategy
that
employs
oxime
carbamate
as
bifunctional
diamination
reagent
in
combination
with
SO2
to
realize
imino-sulfamoylation
of
alkenes.
This
protocol
is
characterized
by
its
mild
conditions,
operational
simplicity,
and
metal-free
nature,
while
demonstrating
broad
functional
group
tolerance
for
Furthermore,
the
application
method
provides
an
accessible
route
diverse
range
β-amino
sulfonamide
derivatives.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(65), P. 8589 - 8592
Published: Jan. 1, 2024
A
novel
and
efficient
method
for
the
preparation
of
diarylmethyl
sulfonamide
derivatives
has
been
achieved
by
visible-light-induced
sulfamoylation
para
-quinone
methides
with
sulfamoyl
chlorides
under
mild
metal-free
conditions.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(20), P. 5784 - 5790
Published: Jan. 1, 2024
The
radical
cascade
cyclization
of
vinyl-tethered
alkenes
has
become
a
promising
tool
for
rapidly
assembling
nonbenzene-fused
cyclic
skeletons
via
the
cracking
alkenyl
C–H
bonds,
but
this
approach
been
limited
to
generate
five-membered
rings.
Facilitated
by
an
electron
donor-acceptor
(EDA)
complex,
efficient
β-trifluoromethylation
and
perfluoroalkylation
of
enamides
with
Togni
reagent
or
perfluoroalkyl
iodides
is
presented
under
transition-metal-free,
photocatalyst-free
mild
reaction
conditions.
Notably,
using
this
strategy,
direct
trifluoromethylation
quinoxalin-2(1
