Chinese Journal of Organic Chemistry,
Год журнала:
2023,
Номер
43(5), С. 1777 - 1777
Опубликована: Янв. 1, 2023
A
convenient
approach
acess
to
boronic
ester
containing
N,O-acetal
structure
has
been
established
through
the
Fe(OTf)3-catalyzed
addition
of
with
organic
boric
acid.A
series
N-O-acetal
compounds
have
successfully
prepared
in
58%~98%
yields.Moreover,
these
retain
property
and
can
be
used
for
coupling
reaction.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(23)
Опубликована: Апрель 2, 2024
The
diversified
synthesis
of
chiral
fluorinated
cyclobutane
derivatives
has
remained
a
difficult
task
in
synthetic
chemistry.
Herein,
we
present
an
approach
for
asymmetric
hydroboration
and
formal
hydrodefluorination
gem-difluorinated
cyclobutenes
through
rhodium
catalysis,
providing
α-boryl
cyclobutanes
monofluorinated
with
excellent
regio-
enantioselectivity,
respectively.
key
to
the
success
two
transformations
relies
on
efficient,
mild
highly
selective
rhodium-catalyzed
HBPin
(pinacolborane),
which
subsequent
addition
base,
catalytic
amount
palladium
some
cases,
results
formation
products
four-membered
ring
retained.
obtained
are
versatile
building
blocks
that
provide
platform
enantioenriched
great
diversity.
ACS Catalysis,
Год журнала:
2024,
Номер
14(20), С. 15790 - 15798
Опубликована: Окт. 10, 2024
Here,
we
report
a
photoredox
and
nickel-catalyzed
cross-electrophile
coupling
strategy
for
the
asymmetric
three-component
1,2-alkylarylation
of
vinyl
boronates
with
(hetero)aryl
bromides
(2°,
3°)-alkyl
redox-active
esters
in
presence
Hantzsch
ester.
With
fluorinated
pyridyl-substituted
chiral
biimidazoline
ligand,
this
reaction
enables
straightforward
access
to
wide
variety
synthetically
valuable
α-aryl
from
readily
available
starting
materials.
This
features
mild
conditions,
broad
substrate
generality,
good
functional
group
tolerance
proceeds
without
using
metal
reductants
or
alkyl
halides.
Furthermore,
alkenyl
halides
other
electron-deficient
alkenes
such
as
acrylates
phosphonates
can
be
applied
successfully.
Preliminary
mechanistic
studies
shed
light
on
potential
pathways
roles
organic
amines.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(43)
Опубликована: Сен. 8, 2023
Abstract
Palladium‐catalyzed
asymmetric
hydrofunctionalization
of
alkenes
is
one
the
most
powerful
and
straightforward
methods
to
forge
a
new
C−H
bond
C−X
(X=C,
N,
O,
F,
Si
etc)
bond,
which
provides
an
efficient
way
obtain
valuable
enantioenriched
molecules
from
cheap
readily
available
feedstocks.
Catalytic
simple
challenging
but
still
highly
sought
after.
This
review
will
mainly
focus
on
recent
advances
in
Palladium
catalyzed
over
past
decade,
including
hydroamination,
hydrooxygenation,
hydrofluorination,
hydrosilylation,
hydroarylation,
hydroalkenylation
hydrocarbonylation.
ACS Catalysis,
Год журнала:
2023,
Номер
14(1), С. 418 - 425
Опубликована: Дек. 20, 2023
Miyaura
borylation
is
widely
recognized
as
one
of
the
most
reliable
methods
for
constructing
an
organoboron
compound.
Reported
herein
Pd(0)-catalyzed
asymmetric
three-component
Heck–Miyaura
with
interception
internal
olefin,
aryldiazonium
salt,
and
diboron
reagent.
This
Heck-triggered
protocol
proceeds
in
a
highly
chemoselective,
diastereoselective,
enantioselective
manner,
thus
allowing
expedient
construction
1,2-diaryl
substituted
β-aminoboronate
esters
derivatives
vicinal
stereogenic
centers.
The
versatility
resulting
benzylic
boronic
allows
their
further
transformation
to
more-intricate
chiral
amines.
Abstract
Catalytic
asymmetric
hydroboration
of
fluoroalkyl‐substituted
alkenes
is
a
straightforward
approach
to
access
chiral
small
molecules
possessing
both
fluorine
and
boron
atoms.
However,
enantioselective
without
elimination
has
been
long‐standing
challenge
in
this
field.
Herein,
copper‐catalyzed
difluoroalkyl‐substituted
internal
with
high
levels
regio‐
enantioselectivities
reported.
The
native
carbonyl
directing
group,
copper
hydride
system,
bisphosphine
ligand
play
crucial
roles
suppressing
the
undesired
fluoride
elimination.
This
atom‐economic
protocol
provides
practical
synthetic
platform
obtain
wide
scope
enantioenriched
secondary
boronates
bearing
difluoromethylene
moieties
under
mild
conditions.
Synthetic
applications
including
functionalization
biorelevant
molecules,
versatile
functional
group
interconversions,
preparation
difluoroalkylated
Terfenadine
derivative
are
also
demonstrated.
ACS Catalysis,
Год журнала:
2024,
Номер
14(6), С. 3977 - 3985
Опубликована: Фев. 28, 2024
Asymmetric
hydroboration
is
among
the
most
powerful
and
straightforward
methods
to
construct
chiral
organoboron
compounds,
which
are
extensively
used
in
natural
products,
bioactive
molecules,
materials
science.
Among
them,
enantioselective
of
a
single
functional
group
has
been
well-established
experienced
significant
advances,
but
asymmetric
multiple
groups
rarely
developed
due
extremely
challenging
chemo-,
regio-,
enantioselectivity
control.
Herein,
we
present
Co-catalyzed
enantio-
regioselective
dihydroboration
enals
achieved
both
C═O
bond
C═C
bond.
This
protocol
features
mild
reaction
conditions,
wide
substrate
scope,
good
tolerance
provides
highly
efficient
method
for
preparation
valuable
1,4-borylethers
their
downstream
products
such
as
1,4-diols
amino
alcohols.
Preliminary
mechanistic
studies
suggested
that
this
involved
tandem
1,2-hydroboration/dissociative
isomerization/asymmetric
process.
Molecules,
Год журнала:
2024,
Номер
29(15), С. 3677 - 3677
Опубликована: Авг. 2, 2024
Organic
fluorides
are
widely
used
in
pharmaceuticals,
agrochemicals,
material
sciences,
and
other
fields
due
to
the
special
physical
chemical
properties
of
fluorine
atoms.
The
synthesis
alkyl
fluorinated
compounds
bearing
multiple
contiguous
stereogenic
centers
is
most
challenging
research
area
synthetic
chemistry
has
received
extensive
attention
from
chemists.
This
review
summarized
important
progress
field
over
past
decade,
including
asymmetric
electrophilic
fluorination
elaboration
substrates
(such
as
allylic
alkylation
reactions,
hydrofunctionalization
Mannich
addition
Michael
aldol
miscellaneous
reactions),
with
an
emphasis
on
methodologies,
substrate
scopes,
reaction
mechanisms.
Chinese Journal of Organic Chemistry,
Год журнала:
2023,
Номер
43(5), С. 1761 - 1761
Опубликована: Янв. 1, 2023
A
cobalt-catalyzed
remote
hydroboration
of
enamines
via
a
sequence
chain
walking
and
in
the
presence
an
earth
abundant
catalyst
commercially
available
ligand
is
reported,
providing
rapid
access
to
borylamines.This
protocol
exhibites
mild
reaction
conditions,
broad
substrate
scope
good
functional
group
compatibility.In
addition,
practicability
potential
synthesis
value
this
were
demonstrated
by
gram
variety
synthetic
transformations
borylamine
products.
Chinese Journal of Organic Chemistry,
Год журнала:
2023,
Номер
43(5), С. 1751 - 1751
Опубликована: Янв. 1, 2023
The
transition
metal-catalyzed
hydroboration
of
alkenes
and
alkynes
is
one
the
most
efficient
way
for
production
boronate
esters.This
type
reaction
100%
atom
economic,
starting
material
readily
available,
products
are
diverse.It
noticed
that
known
catalytic
systems
based
on
late-transition-metals
such
as
Rh,
Ir,
Pd,
Pt,
Co,
Fe
Cu.The
use
early-transition-metals
zirconium
titanium,
other
hand,
very
scarce.In
this
short
review,
development
application
in
titanium
mediated
alkene
alkyne
summarized,
research
trends
area
also
discussed.