Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
135(51)
Published: Nov. 8, 2023
Abstract
Sulfur
monoxide
(SO)
is
a
highly
reactive
species
that
cannot
be
isolated
in
bulk.
However,
SO
can
play
pivotal
role
as
fundamental
building
block
organic
synthesis.
Reported
herein
the
design
and
application
of
sulfinylhydrazine
reagent
an
easily
prepared
sulfur
surrogate.
We
show
facile
thermal
transfer
from
this
to
dienes
where
reaction
using
mechanistic
probe
suggests
generation
singlet
SO.
Combined
with
Grignard
reagents
appropriate
carbon
or
nitrogen
electrophiles,
serves
effective
“SO”
donor
enable
one‐pot,
three‐component
synthesis
sulfoxides
sulfinamides.
Acta Chimica Sinica,
Journal Year:
2023,
Volume and Issue:
81(11), P. 1522 - 1522
Published: Jan. 1, 2023
Chiral
molecules
are
ubiquitous
in
nature
and
play
an
important
role
natural
products,
pharmaceuticals,
agriculture,
advanced
materials,
as
well
living
organisms.Therefore,
the
development
of
efficient
strategies
to
enable
facile
construction
enantiopure
chiral
compounds
atom-and
step-economical
manner
is
great
importance.The
enantioselective
functionalization
C-H
bonds
without
multi-steps
transformation
arguably
one
most
powerful
straightforward
fulfill
this
goal.This
emerging
research
field
has
been
rapidly
developed
with
innovation
various
catalysts
and/or
ligands
recent
years.In
particular,
significant
advances
have
achieved
palladium-catalyzed
C(sp
3
)-H
bonds,
streamlining
concise
from
readily
available
hydrocarbon
feedstocks.The
stereoselective
assistance
ligand
form
a
palladacycle
intermediate,
which
could
be
transformed
into
chemical
functionalized
compounds,
attracted
tremendous
attention.Thus,
perspective
summarizes
on
palladium(II)-catalyzed
via
asymmetric
palladation.According
type
classified
several
sections,
including
methyl
methylene
constrained
cycloalkanes,
adjacent
α-heteroatom,
benzylic
unbiased
bonds.The
emphasis
focuses
discussion
philosophy
developing
novel
mode
stereocontrol.The
remaining
limitations
challenges
regarding
chemo-and
control
also
discussed.Further
new
catalytic
systems
expected
address
these
issues
expands
scope
synthetic
strategy.We
anticipate
that
might
inspire
more
efforts
strategy
find
wide
applications
synthesis
complicated
molecules,
such
products
drugs.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(9), P. 7213 - 7219
Published: April 24, 2024
Transition-metal-catalyzed
enantioselective
C–H
functionalization
has
emerged
as
a
promising
method
for
the
synthesis
of
P-stereogenic
phosphorus
compounds.
However,
previous
reports
are
limited
to
C(sp2)–H
bonds
aryl
phosphine
derivatives.
Herein,
Pd(II)-catalyzed
arylation
more
challenging
C(sp3)–H
toward
dialkylphosphinamides
is
achieved
through
desymmetrization
gem-diethyl
groups.
Various
obtained
with
high
enantioselectivities
using
3,3′-CN2-H8-BINOL
chiral
ligand.
The
synthetic
potential
this
methodology
highlighted
by
gram-scale
preparation
and
further
derivatizations.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(10), P. 7762 - 7770
Published: May 3, 2024
The
4-aryl-2-pyridone
scaffold
is
considered
to
be
a
privileged
pharmacophore.
Diversity-oriented
synthesis
of
its
derivatives
pressing
demand
within
the
field
medicinal
chemistry.
Herein,
we
report
site-selective
C–H
arylation
2-pyridones
via
palladium/norbornene
cooperative
catalysis.
success
this
research
based
on
nucleophilicity
and
metalation
properties
exhibited
by
C5
position
in
2-pyridones,
an
activated
norbornene
that
was
employed
capture
C5-palladation
intermediate
transfer
it
C4
position,
resulting
highly
specific
at
position.
This
methodology
showcases
remarkable
compatibility
with
readily
available
aryl
bromides,
enabling
efficient
diverse
range
functional
scaffolds
(46
examples)
notable
site
selectivity,
which
will
very
useful
drug
discovery.
Furthermore,
approach
successfully
utilized
for
economically
viable
perlolidine
analogues.
Density
theory
calculations
revealed
preference
bond
activation
2-pyridones.
In
addition,
insights
into
mechanism
suggest
oxidative
addition
reductive
elimination
bromides
are
crucial
steps
conversion.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
27(10), P. 2509 - 2514
Published: March 5, 2025
Chiral
cyclobutanamide
is
a
privileged
scaffold
in
drug
discovery.
Here,
we
describe,
for
the
first
time,
synthesis
of
axially
chiral
cyclobutanamides
via
phosphoric
acid-catalyzed
enantioselective
condensation
between
N-arylcarbamyl
cyclobutanones
and
hydroxylamines.
Rational
substrate
design,
incorporating
an
amide
moiety
(CONHR)
into
cyclobutanone
backbone
formation
multi-hydrogen
bonding
network
involving
N-H
this
portion,
responsible
excellent
enantioselectivity
achieved
stereodetermining
dehydration
process,
which
supported
by
detailed
mechanistic
study.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(13)
Published: Feb. 15, 2024
Abstract
Direct
C−H
functionalization
is
an
important
strategy
for
the
rapid
synthesis
of
valuable
organic
molecules.
Radical‐involved
remote
C(sp
3
)‐H
based
on
hydrogen
atom
transfer
(HAT)
becomes
method
enabling
selective
direct
transformation
bonds
at
specific
distal
position(s).
In
recent
years,
copper‐catalyzed
fluoroamide‐directed
bond
through
intramolecular
HAT
has
served
as
a
robust
and
elegant
assembly
variety
functionalized
(sulfon)amides
related
derivatives.
This
review
focuses
advances
in
this
area.
These
transformations
proceed
effectively
with
high
selectivities
good
functional
group
compatibility
under
mild
conditions.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(51)
Published: Nov. 8, 2023
Abstract
Sulfur
monoxide
(SO)
is
a
highly
reactive
species
that
cannot
be
isolated
in
bulk.
However,
SO
can
play
pivotal
role
as
fundamental
building
block
organic
synthesis.
Reported
herein
the
design
and
application
of
sulfinylhydrazine
reagent
an
easily
prepared
sulfur
surrogate.
We
show
facile
thermal
transfer
from
this
to
dienes
where
reaction
using
mechanistic
probe
suggests
generation
singlet
SO.
Combined
with
Grignard
reagents
appropriate
carbon
or
nitrogen
electrophiles,
serves
effective
“SO”
donor
enable
one‐pot,
three‐component
synthesis
sulfoxides
sulfinamides.
