Nature Communications,
Год журнала:
2022,
Номер
13(1)
Опубликована: Ноя. 3, 2022
The
development
of
novel
methodologies
for
the
introduction
sulfoxonium
group
under
mild
conditions
is
appealing
but
remains
underexplored.
Herein
we
report
synthesis
a
class
hypervalent
iodine
reagents
with
transferrable
group.
These
compounds
enable
mixed
iodonium-sulfoxonium
ylide
reactivity.
well-defined
are
examined
in
visible-light-promoted
cyclization
reactions
wide
range
unsaturated
bonds
including
alkenes,
alkynes,
nitriles,
and
allenes.
Two
distinct
pathways
identified,
which
controlled
by
substituent
bond.
cycloaddition
protocol
features
simple
operation,
reaction
conditions,
excellent
functional
tolerance,
affording
broad
sulfoxonium-containing
cyclic
structures
moderate
to
yields.
Furthermore,
sufoxonium
product
can
be
transformed
into
diverse
groups
structural
motifs
via
single
electron
transfer
transition-metal
catalysis.
JACS Au,
Год журнала:
2023,
Номер
3(1), С. 252 - 260
Опубликована: Янв. 3, 2023
Herein,
we
describe
the
development
of
a
new
strategy
for
synthesis
unsaturated
oligoesters
via
sequential
metal-
and
reagent-free
insertion
vinyl
sulfoxonium
ylides
into
O-H
bond
carboxylic
acid.
Like
two
directional
coupling
amino
acids
(N-
to
C-terminal
C-
N-terminal)
in
peptide
synthesis,
present
approach
offers
both
directions
synthesize
oligoesters.
The
addition
ylide
(acid
iteration
sequence)
one
direction
(ylide
another
yield
(Z)-configured
To
perform
this
iteration,
have
developed
highly
regioselective
X-H
(X
=
O,
N,
C,
S,
halogen)
acids,
thiols,
phenols,
amines,
indoles,
halogen
under
metal-free
reaction
conditions.
is
applied
broad
range
substrates
(>50
examples,
up
99%
yield)
eight
iterative
sequences.
Mechanistic
studies
suggest
that
rate-limiting
step
depends
on
type
insertion.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(11), С. 3234 - 3241
Опубликована: Янв. 1, 2024
Herein,
we
present
a
cascade
O–H
double
insertion
reaction
between
I
(III)
/S
(VI)
-ylides,
carboxylic
acids,
and
alcohols
under
metal-free
conditions,
enabling
the
modular
synthesis
of
unsymmetrical
α,α-
O
,
-substituted
ketones.
Organic Letters,
Год журнала:
2024,
Номер
26(27), С. 5811 - 5816
Опубликована: Июнь 28, 2024
A
practical
strategy
for
the
construction
of
diverse
phosphonyl
and
thiofunctionalized
sulfoxonium
ylides
via
controllable
monofunctionalization
hybrid
I(III)/S(VI)
is
presented.
This
process
allows
efficient
P–H
insertion
under
Cu
catalysis,
enabling
synthesis
ylides,
whereas
reaction
with
sulfur-containing
reagents
including
AgSCF3,
KSC(S)OR,
KSCN
mild
conditions
resulted
in
α-trifluoromethylthiolation,
dithiocarbanation,
thiocyanation
accordingly.
Of
note,
wide
substrate
compatibility
(108
examples),
excellent
efficiency
(up
to
99%
yield),
gram-scale
experiments,
various
product
derivatizations
highlight
synthetic
utility
this
protocol.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(8), С. 1744 - 1750
Опубликована: Фев. 22, 2024
Abstract
The
transmetalation
triggered
rhodium‐catalyzed
C−H
bond
activation
and
tandem
annulation
of
2‐biphenylboronic
acids
with
sulfoxonium
ylides
or
iodonium
has
been
developed.
Various
products
phenanthrenes
were
constructed
under
redox‐neutral
conditions
in
34–86%
yields.
Several
mechanism
exploration
experiments
derivatization
reactions
conducted
sequence
to
gain
a
deeper
understanding
the
process
potential
this
transformation.
It
offers
an
alternative
approach
for
synthesis
phenanthrene
derivatives.
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(5), С. 1436 - 1442
Опубликована: Янв. 21, 2021
Abstract
A
highly
efficient
cascade
Rh(III)‐catalyzed
C−H
activation/intramolecular
chemodivergent
cyclization
reaction
of
N‐carbamoylindoles
and
sulfoxonium
ylides
has
been
successfully
achieved
for
the
first
time.
This
synergistic
process
provides
rapid
access
to
functionalized
dihydropyrimidoindolone
tricyclic
[1,3]oxazino[3,4‐
a
]indol‐1‐ones
skeletons
under
redox
neutral
conditions
with
broad
substrate
scope
remarkable
functional‐group
compatibility.
Further
late‐stage
modification
structurally
complex
drug
molecules
mechanistic
studies
were
also
accomplished.
magnified
image
Chinese Journal of Chemistry,
Год журнала:
2021,
Номер
39(12), С. 3211 - 3218
Опубликована: Авг. 12, 2021
Abstract
Our
recently
studies
on
three
types
of
reactions
with
hydrogen
transfer
as
a
key
step,
including
catalytic
asymmetric
proton
using
“chiral
shuttle”,
B—H
bond
insertion
containing
atom
transfer,
and
iron‐catalyzed
hydrosilylation
hydride
were
briefly
introduced.
What
is
the
most
favorite
original
chemistry
developed
in
your
research
group?
The
discovery
reaction.
How
do
you
get
into
this
specific
field?
Could
please
share
some
experiences
our
readers?
reaction
was
serendipitous
result
during
we
pursuing
other
carbene
reactions.
My
lesson
project
that
may
come
from
bold
hypothesis,
cautious
verification,
appropriate
evaluation
unexpected
results.
supervise
students?
Try
my
best
to
stimulate
their
enthusiasm
for
innovation,
provide
them
strongest
supports,
explore
unknown
partner.
important
personality
scientific
research?
Passion
self‐actualization
curiosity.
keep
balance
between
family?
Travel
family
regularly
try
progresses
them.
Angewandte Chemie International Edition,
Год журнала:
2021,
Номер
60(45), С. 24214 - 24219
Опубликована: Сен. 3, 2021
The
scarcity
of
reliable
methods
for
synthesizing
chiral
gem-diarylmethine
borons
limits
their
applications.
Herein,
we
report
a
method
highly
enantioselective
dirhodium-catalyzed
B-H
bond
insertion
reactions
with
diaryl
diazomethanes
as
carbene
precursors.
These
afforded
borane
compounds
in
high
yield
(up
to
99
%
yield),
activity
(turnover
numbers
up
14
300),
enantioselectivity
ee)
and
showed
unprecedented
broad
functional
group
tolerance.
synthesized
by
this
could
be
efficiently
transformed
into
methanol,
methyl
amine,
triaryl
methane
derivatives
good
stereospecificity.
Mechanistic
studies
suggested
that
the
adduct
coordinated
rhodium
catalyst
thus
interfered
decomposition
diazomethane,
(generated
from
diazomethane)
was
most
likely
rate-determining
step.
Organic & Biomolecular Chemistry,
Год журнала:
2021,
Номер
19(26), С. 5767 - 5771
Опубликована: Янв. 1, 2021
A
copper-catalyzed
P–H
insertion
reaction
between
sulfoxonium
ylides
and
H-phosphorus
oxides
has
been
developed
to
synthesize
α-phosphonyl
carboxylate
derivatives.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(9), С. 1457 - 1464
Опубликована: Апрель 14, 2023
Abstract
In
this
study,
Rh(III)‐catalyzed
C−H
bifunctionalization
and
direct
vinylene
annulation
of
sulfoxonium
ylides
N
‐carbamoylindoles
with
carbonate
was
accomplished,
which
afforded
a
series
naphthalenones
containing
β‐ketosulfoxonium
ylide
moiety,
isocoumarins,
pyrimidones.
This
protocol
featured
mild
conditions,
broad
substrate
scope,
functional‐groups
compatibility.
addition,
related
applications
preliminary
mechanistic
exploratory
were
also
investigated
magnified
image
ChemCatChem,
Год журнала:
2021,
Номер
13(20), С. 4299 - 4312
Опубликована: Авг. 11, 2021
Abstract
Carbene
B−H
insertion
reactions
represent
an
efficient
method
for
C−B
bond
formation,
which
have
experienced
great
advances
in
recent
years.
Free
and
metal
carbene
into
bonds
based
on
diazo
nondiazo
precursors,
including
α‐diazoesters,
α‐diazoketones,
hydrazones,
chloroforms,
acylsilanes,
alkenyl
triflates,
alkynes
sulfoxonium
ylides
been
well
studied.
The
development
of
this
chemistry
complements
existing
formation
strategies
terms
substrate
scope,
selectivity
product
diversity.
Notably,
the
catalytic
enantioselective
enable
easy
access
to
challenging
but
important
chiral
organoboron
compounds.
This
review
provides
a
timely
overview
research
topic.
Typical
achievements
reaction
methodologies,
plausible
mechanisms,
as
applications
synthesis
bioactive
molecules
are
summarized.
