ACS Catalysis,
Journal Year:
2017,
Volume and Issue:
7(12), P. 8200 - 8204
Published: Oct. 24, 2017
The
copper-catalyzed
reaction
of
allenes
with
bis(pinacolato)diboron
and
acyl
electrophiles
is
reported.
In
this
transformation,
fluorides
have
been
proven
to
be
more
efficient
coupling
partners
than
their
chloride
or
carboxylate
analogues.
optimized
conditions
employed
were
shown
compatible
a
range
commonly
used
functional
groups,
thereby
allowing
the
formation
library
β-boryl
β,γ-unsaturated
ketones
by
varying
nature
allene
fluoride
substrates.
Chemical Reviews,
Journal Year:
2016,
Volume and Issue:
116(16), P. 9091 - 9161
Published: July 19, 2016
Although
known
for
over
90
years,
only
in
the
past
two
decades
has
chemistry
of
diboron(4)
compounds
been
extensively
explored.
Many
interesting
structural
features
and
reaction
patterns
have
emerged,
more
importantly,
these
now
feature
prominently
both
metal-catalyzed
metal-free
methodologies
formation
B-C
bonds
other
processes.
Chemical Society Reviews,
Journal Year:
2018,
Volume and Issue:
47(19), P. 7477 - 7494
Published: Jan. 1, 2018
The
diverse
applications
of
copper-catalyzed
borylation,
which
has
become
an
essential
strategy
in
modern
synthetic
organic
chemistry,
are
reviewed
and
illustrated.
Angewandte Chemie International Edition,
Journal Year:
2017,
Volume and Issue:
56(39), P. 11700 - 11733
Published: May 18, 2017
Abstract
Non‐racemic
chiral
boronic
esters
are
recognised
as
immensely
valuable
building
blocks
in
modern
organic
synthesis.
Their
stereospecific
transformation
into
a
variety
of
functional
groups—from
amines
and
halides
to
arenes
alkynes—along
with
their
air
moisture
stability,
has
established
them
an
important
target
for
asymmetric
Efforts
towards
the
stereoselective
synthesis
secondary
tertiary
alkyl
have
spanned
over
five
decades
underpinned
by
wealth
reactivity
platforms,
drawing
on
unique
varied
boron.
This
Review
summarizes
strategies
esters,
from
seminal
hydroboration
methods
H.
C.
Brown
current
state
art.
Journal of the American Chemical Society,
Journal Year:
2015,
Volume and Issue:
137(43), P. 13760 - 13763
Published: Oct. 13, 2015
A
cooperative
Cu/Pd-catalyzed
asymmetric
three-component
reaction
of
styrenes,
B2(pin)2,
and
allyl
carbonates
was
reported.
This
reaction,
in
the
presence
chiral
CuOAc/SOP
achiral
Pd(dppf)Cl2
catalysts,
occurs
smoothly
with
high
enantioselectivities
(up
to
97%
ee)
.
The
allylboration
products,
which
contain
alkene
(or
diene)
unite
alkylboron
group,
are
easily
functionalized.
utility
this
protocol
demonstrated
through
synthesis
an
antipsychotic
drug,
(−)-preclamol.
ACS Catalysis,
Journal Year:
2020,
Volume and Issue:
10(19), P. 11578 - 11622
Published: Aug. 25, 2020
Organoboronates
represent
a
cornerstone
functional
group
in
modern
synthesis
owing
to
their
unique
reactivity
and
divergent
synthetic
capability.
Copper
catalysis
has
become
one
of
the
most
powerful
methods
stereoselectively
install
boron
across
diverse
π-systems.
Additionally,
this
method
affords
tremendous
versatility
enabled
by
difunctionalization
π-system
addition
an
electrophile.
This
review
covers
known
electrophiles
intercept
catalytic
intermediates
borylative
strategies
that
have
been
reported
up
end
May
2020.
Angewandte Chemie International Edition,
Journal Year:
2016,
Volume and Issue:
56(3), P. 851 - 855
Published: Dec. 21, 2016
Abstract
A
method
for
the
catalytic
enantioselective
arylboration
of
alkenylarenes
is
disclosed.
The
reaction
leads
to
formation
1,1‐diarylalkanes
that
also
incorporate
an
additional
pinacol
boronic
ester
which
can
be
easily
transformed
a
variety
groups.
products
are
formed
with
excellent
diastereoselectivities
and
enantioselectivities.
Angewandte Chemie International Edition,
Journal Year:
2015,
Volume and Issue:
54(44), P. 12957 - 12961
Published: Sept. 4, 2015
Abstract
A
novel
copper‐catalyzed
regiodivergent
alkylboration
of
alkenes
with
bis(pinacolato)diboron
and
alkyl
halides
has
been
developed.
The
regioselectivity
the
was
controlled
by
subtle
differences
in
ligand
structure.
reaction
thus
enables
practical,
synthesis
two
different
boronic
esters
complex
structures
from
a
single
alkene.
Synthesis,
Journal Year:
2017,
Volume and Issue:
49(15), P. 3323 - 3336
Published: July 11, 2017
The
Zweifel
olefination
is
a
powerful
method
for
the
stereoselective
synthesis
of
alkenes.
reaction
proceeds
in
absence
transition-metal
catalyst,
instead
taking
place
by
iodination
vinyl
boronate
complexes.
Pioneering
studies
into
this
were
reported
1967
and
short
review
summarizes
developments
field
over
past
50
years.
An
account
how
was
modified
to
enable
coupling
robust
air-stable
boronic
esters
presented
followed
summary
current
state
art
field,
including
stereodivergent
alkynylation.
Finally,
selected
applications
target-oriented
are
reviewed.
1
Introduction
2.1
Olefination
Vinyl
Boranes
2.2
Borinic
Esters
2.3
Extension
Boronic
3.1
an
Unsubstituted
Group
3.2
Coupling
α-Substituted
Partners
3.3
Syn
Elimination
4
Natural
Product
Synthesis
5
Conclusions
Outlook
Accounts of Chemical Research,
Journal Year:
2020,
Volume and Issue:
53(8), P. 1605 - 1619
Published: July 24, 2020
ConspectusThe
oxindole
scaffold
is
a
privileged
structural
motif
that
found
in
variety
of
bioactive
targets
and
natural
products.
Moreover,
derivatives
the
structure
are
widely
present
number
biologically
relevant
compounds
key
intermediates
synthesis
diverse
products
pharmaceuticals.
Therefore,
novel
methods
to
obtain
oxindoles
remain
high
priority
synthetic
organic
chemistry.Over
past
several
decades,
transition-metal-catalyzed
methodologies
have
been
applied
toward
heterocycles.
A
detailed
mechanistic
understanding
facilitates
disruption
traditional
catalytic
pathways
access
useful
intermediates.
The
strategies
employed
generally
revolved
around
generation
high-energy
organometallic
intermediates,
which
undergo
cyclization
reactions
through
domino
processes.
Domino
therefore
attractive,
as
they
allow
facile
functionalized
containing
all-carbon
quaternary
centers
or
tetrasubstituted
olefins
with
chemo-
stereoselectivities.
Furthermore,
these
developed
can
often
be
easily
syntheses
other
related
scaffolds.In
this
Account,
we
discuss
three
unique
our
group
has
leveraged
for
valuable
scaffolds.
first
section
Account
outlines
use
an
initial
oxidative
addition
C(sp2)–X
bond,
followed
by
migratory
insertion,
yielding
neopentyl
species
amenable
subsequent
functionalizations.
From
reactive
metal
species,
reported
C–X
reductive
eliminations,
anionic
capture
cascade
reactions,
intramolecular
C–H
functionalization
second
summarizes
group's
findings
on
1,2-insertions
metal–nucleophile
across
unsaturation,
generating
intermediate;
tethered
electrophiles
form
desired
heterocyclic
core.
We
explored
wide
array
transition
metal-catalyzed
using
approach,
including
rhodium-catalyzed
conjugate
additions,
asymmetric
copper-catalyzed
borylcupration,
palladium(II)-catalyzed
chloropalladation
protocol.
final
details
dual-metal
catalysis
perform
functionalization–allylation
reaction.
Throughout
provide
studies
better
enabled
processes.Overall,
exploiting
reactivity
palladium,
nickel,
copper,
rhodium,
ruthenium
catalysts
develop
On
basis
utility,
diversity,
applicability
developed,
believe
will
prove
highly
important
inspire
further
development
various
