Crystal Growth & Design,
Journal Year:
2023,
Volume and Issue:
23(4), P. 2661 - 2674
Published: March 23, 2023
The
simultaneous
binding
of
a
molecular
entity
through
two
interactions
is
frequently
pursued
recognition
mode
due
to
the
advantages
it
offers
in
securing
self-assembly.
Here,
we
report
how
planarity
benzothienoiodolium
(BTI)
cation
allows
for
preorganizing
plane
hydrogen,
halogen,
and
chalcogen
bonds
(HBs,
XBs,
ChBs,
respectively)
formed
by
phenyl
iodolium
iodine,
thienyl
sulfur.
Crystallographic
analyses
some
BTI
salts
show
this
interaction
coplanarity
enables
their
coupling
point
toward
single
anion
that
coordinated
via
supramolecular
heteroditopic
synthon
XB/HB
or
XB/ChB,
latter
observed
here
first
time.
These
synthons
adopt
Janus-like
arrangement
around
iodine.
information
suggests
act
synergistically,
e.g.,
when
resulting
unusually
short
ChBs
Determination
electrostatic
potential,
Bader's
quantum
theory
"atoms-in-molecules"
analysis,
natural
bond
orbital
investigations
give
on
nature
energetic
aspects
contacts
crystals.
Chemical Reviews,
Journal Year:
2023,
Volume and Issue:
123(4), P. 1364 - 1416
Published: Jan. 17, 2023
Hypervalent
aryliodoumiums
are
intensively
investigated
as
arylating
agents.
They
excellent
surrogates
to
aryl
halides,
and
moreover
they
exhibit
better
reactivity,
which
allows
the
corresponding
arylation
reactions
be
performed
under
mild
conditions.
In
past
decades,
acyclic
aryliodoniums
widely
explored
However,
unmet
need
for
is
improvement
of
their
notoriously
low
reaction
economy
because
coproduced
iodides
during
often
wasted.
Cyclic
have
intrinsic
advantage
in
terms
economy,
started
receive
considerable
attention
due
valuable
synthetic
applications
initiate
cascade
reactions,
can
enable
construction
complex
structures,
including
polycycles
with
potential
pharmaceutical
functional
properties.
Here,
we
summarizing
recent
advances
made
research
field
cyclic
aryliodoniums,
nascent
design
aryliodonium
species
applications.
First,
general
preparation
typical
diphenyl
iodoniums
described,
followed
by
heterocyclic
monoaryl
iodoniums.
Then,
initiated
arylations
coupled
subsequent
domino
summarized
construct
polycycles.
Meanwhile,
building
biaryls
axial
atropisomers
discussed
a
systematic
manner.
Finally,
very
advance
employed
halogen-bonding
organocatalysts
described.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(15), P. 10199 - 10207
Published: July 20, 2022
Sulfonium
and
selenonium
salts,
represented
by
S-aryl
dibenzothiophenium
Se-aryl
dibenzoselenophenium
triflates,
were
found
to
exhibit
remarkable
catalytic
activity
in
the
model
Groebke–Blackburn–Bienaymé
reaction.
Kinetic
analysis
density
functional
theory
(DFT)
calculations
indicated
that
their
effect
is
induced
ligation
of
reaction
substrates
σ-holes
on
S
or
Se
atom
cations.
The
experimental
data
although
10-fold
excess
chloride
totally
inhibits
sulfonium
salt
remains
catalytically
active,
which
can
be
explained
experimentally
lower
binding
constant
derivative
comparison
with
analogue.
Both
types
salts
than
dibenziodolium
species.
The Journal of Physical Chemistry A,
Journal Year:
2024,
Volume and Issue:
128(3), P. 507 - 527
Published: Jan. 12, 2024
As
important
noncovalent
interactions,
halogen
bonds
have
been
widely
used
in
material
science,
supramolecular
chemistry,
medicinal
organocatalysis,
and
other
fields.
In
the
past
15
years,
bond
catalysis
has
become
a
developed
field
organocatalysis
for
catalysts'
advantages
of
being
environmentally
friendly,
inexpensive,
recyclable.
Halogen
can
induce
various
organic
reactions,
powerful
alternative
to
fully
explored
hydrogen
catalysis.
From
physical
chemistry
view,
this
perspective
provides
an
overview
latest
progress
key
examples
via
activation
lone
pair
systems
functional
group,
π
systems,
metal
complexes.
The
research
progresses
by
our
group
were
also
introduced.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(8), P. 1112 - 1139
Published: Feb. 28, 2023
Abstract
Cyclic
diaryliodoniums
are
an
important
class
of
high‐valent
aromatic
iodine
reagents
for
the
synthesis
various
axially
chiral
biaryls
and
biaryl
compounds.
Moreover,
transition‐metal‐catalyzed
annulation
has
been
established
construction
heterocyclic
rings
ladder‐type
π‐conjugated
polycyclic
hydrocarbons
with
readily
available
cyclic
as
starting
materials.
As
halogen‐bonding
donors,
aryliodoniums
have
explored
organocatalysts
in
a
variety
organic
reactions.
In
this
review,
application
progress
systematically
outlined,
which
highlights
recent
developments
reactions
diaryliodoniums,
including
synthetic
application,
limitations
reaction
mechanisms
representative
cascade
to
provide
insights
development
prospects
diaryliodoniums.
magnified
image
Chemical Science,
Journal Year:
2022,
Volume and Issue:
13(22), P. 6532 - 6540
Published: Jan. 1, 2022
A
revised
bonding
model
for
diarylhalonium
salts,
that
involves
partial
s-orbital
contribution,
provides
new
insight
into
periodic
trends
in
structure
and
reactivity.
Beilstein Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
20, P. 1839 - 1879
Published: Aug. 1, 2024
The
Groebke–Blackburn–Bienaymé
(GBB)
three-component
reaction,
discovered
in
1998,
is
a
very
efficient
strategy
to
assemble
imidazo[1,2-
]-heterocycles
starting
from
amidines,
aldehydes
and
isocyanides.
This
review
aims
exhaustively
describe
innovative
aspects
of
this
reaction
achieved
during
the
last
five
years,
classifies
them
into
categories:
synthetic
methods,
building
blocks,
scaffolds,
biological
activities
physical
properties.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(38), P. 7632 - 7639
Published: Jan. 1, 2022
This
theoretical
study
sheds
light
on
the
relative
catalytic
activity
of
pnictonium,
chalconium,
and
halonium
salts
in
reactions
involving
elimination
chloride
electrophilic
activation
a
carbonyl
group.
DFT
calculations
indicate
that
for
cationic
aromatic
onium
salts,
values
electrostatic
potential
heteroatom
σ-holes
gradually
increase
from
pnictogen-
to
halogen-containing
species.
The
higher
halogen
atoms
result
overall
these
species,
but
case
pnictonium
chalconium
cations,
weak
interactions
side
groups
provide
an
additional
stabilization
effect
reaction
transition
states.
Based
upon
quantum-chemical
calculations,
phosphonium(V)
arsenonium(V)
is
expected
be
too
low
obtain
effective
noncovalent
organocatalytic
compounds,
whereas
stibonium(V),
telluronium(IV)
iodonium(III)
exhibit
application
as
organocatalysts.
