European Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
2022(32)
Published: July 25, 2022
Abstract
Halogens
play
a
crucial
part
in
synthetic
organic
chemistry.
Halo‐cyclized
products
hold
numerous
applications
the
pharmaceutical
industries,
agrochemicals,
natural
product
synthesis,
and
material
Thus,
this
review
will
discuss
role
of
various
catalysts,
such
as
from
metal‐catalysts
to
organocatalysts,
under
different
conditions
synthesize
halocyclized
products.
The
synthesis
catalytic
mechanisms
underlying
asymmetric
transformations
also
be
covered
by
emphasizing
enantioselectivities,
diastereoselectivities,
regioselectivities
existing
pieces
literature.
Chemical Science,
Journal Year:
2022,
Volume and Issue:
13(15), P. 4327 - 4333
Published: Jan. 1, 2022
We
report
a
previously
unknown
disconnection
approach
to
valuable
fluorinated
tertiary
stereocenters
based
on
the
skeletal
modification
of
1,1-disubstituted
alkenes
by
Rh-catalyzed
carbyne
transfer.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(23), P. 3974 - 4005
Published: Oct. 20, 2022
Abstract
Halogen
(fluorine,
chlorine,
bromine,
iodine)
or
chalcogen
(sulfur,
selenium)‐containing
heterocycles
are
widely
recognized
as
key
building
blocks
in
many
natural
products
and
bioactive
targets.
Catalytic
asymmetric
halogenation/chalcogenation
of
carbon‐carbon
unsaturated
bonds
via
onium
ion
transformations
efficient
methods
to
obtain
diverse
chiral
heterocyclic
backbones.
In
the
past
few
years,
catalytic
enantioselective
versions
halo/thio/seleno‐functionalizations
with
various
halogen
electrophiles
have
experienced
constant
development.
This
review
highlights
those
advances
preparing
functionalized
promoted
by
organocatalysts
metal‐based
catalysts.
magnified
image
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(20), P. 4163 - 4180
Published: Jan. 1, 2023
A
number
of
organic
transformations
have
been
achieved
using
hypervalent
iodine
reagents
under
mild
reaction
conditions.
The
use
these
as
chiral
organocatalyst
exhibited
highly
selective
asymmetric
reactions.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(19)
Published: March 8, 2023
Homologation
of
trisubstituted
fluoroalkenes
followed
by
allylboration
aldehyde,
ketone
and
imine
substrates
is
suitable
for
synthesis
β-fluorohydrin
amine
products.
In
the
presence
(R)-iodo-BINOL
catalyst
enantioselectivities
up
to
99
%
can
be
achieved
formation
a
single
stereoisomer
with
adjacent
stereocenters,
which
one
tertiary
C-F
center.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
27(4), P. 1030 - 1035
Published: Jan. 20, 2025
Compared
with
the
energetically
favorable
5-
or
6-membered
fluoro-functionalized
heterocycles,
construction
of
medium-sized
fluoro-heterocycles
is
relatively
under-researched
because
their
inherently
unfavorable
enthalpic
and
entropic
nature.
Based
on
rational
design
DFT
calculations,
a
novel
photocatalytic
difluoromethyl
radical-initiated
intramolecular
7-endo-trig
cyclization
was
realized,
thus
affording
sustainable
route
for
synthesis
challenging
N-heterocycles.
Depending
atomic
dipole
moment
corrected
Hirshfeld
population
(ADCH)
charge
chemoselective
6-exo-trig
radical
cyclizations
were
further
replenished.
Large-scale
derivatization
demonstrated
wide
utility
this
method.
Natural Sciences,
Journal Year:
2021,
Volume and Issue:
1(2)
Published: Aug. 5, 2021
Abstract
The
efficient
construction
of
γ
‐chirogenic
amines
has
been
realized
via
asymmetric
hydrogenation
‐branched
N
‐phthaloyl
allylamines
by
using
a
bisphosphine‐Rh
catalyst
bearing
large
bite
angle.
desired
products
possessing
different
‐substituents
were
obtained
in
quantitative
yields
and
with
excellent
enantioselectivities
(up
to
>99%
ee).
This
protocol
provides
practical
method
for
the
preparation
amine
derivatives
such
as
famous
antidepressant
drug
Fluoxetine
50000
S/C).
mechanistic
calculations
show
an
unusual
P‐Rh‐P
trans
‐chelating
pattern
weak
interaction‐promoted
activation
mode
which
are
completely
from
traditional
cis
coordination‐promoted
metal‐catalyzed
hydrogenations.
Key
points
Novel
methodology
was
developed
synthesis
γ‐chirogenic
amines.
New
synthetic
route
well‐known
Fluoxetine.
Unusual
mechanism
information
found
bidentate
bisphosphine‐Rh‐catalyzed
hydrogenation.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
62(1)
Published: Nov. 8, 2022
Abstract
A
catalysis‐based
regioselective
1,4‐fluorofunctionalization
of
trifluoromethyl
substituted
1,3‐dienes
has
been
developed
to
access
compact,
highly
functionalized
products.
The
process
allows
E
,
Z
‐mixed
dienes
be
processed
a
single
‐alkene
isomer,
and
leverages
an
inexpensive
operationally
convenient
I(I)/I(III)
catalysis
platform.
first
example
catalytic
1,4‐difluorination
is
disclosed
subsequently
evolved
enable
1,4‐hetero‐difunctionalization,
which
δ‐fluoro‐alcohol
amine
derivatives
forged
in
operation.
protocol
compatible
with
variety
nucleophiles
including
fluoride,
nitriles,
carboxylic
acids,
alcohols
even
water
thereby
allowing
products,
stereocenter
bearing
both
C(sp
3
)−F
)−CF
groups,
generated
rapidly.
Scalability
(up
mmol),
facile
post‐reaction
modifications
are
demonstrated
underscore
the
utility
method
expanding
organofluorine
chemical
space.
