Angewandte Chemie International Edition,
Год журнала:
2019,
Номер
58(39), С. 13860 - 13864
Опубликована: Июль 9, 2019
The
direct
and
selective
functionalization
of
relatively
simple
readily
accessible
precursors
to
produce
highly
functionalized
alkyl
boronates
is
a
synthetically
useful
process.
Herein
we
report
NiH-catalyzed
remote
hydroarylation
process
that
can,
through
synergistic
combination
chain
walking
subsequent
cross-coupling,
introduce
an
aryl
group
at
the
adjacent
carbon
atom
under
mild
conditions.
By
means
preliminary
experiment
with
moderate
enantioselectivity,
it
was
shown
asymmetric
version
could
also
be
realized.
Chemical Reviews,
Год журнала:
2021,
Номер
121(21), С. 13238 - 13341
Опубликована: Окт. 7, 2021
Organoboron
reagents
represent
a
unique
class
of
compounds
because
their
utility
in
modern
synthetic
organic
chemistry,
often
affording
unprecedented
reactivity.
The
transformation
the
carbon–boron
bond
into
carbon–X
(X
=
C,
N,
and
O)
stereocontrolled
fashion
has
become
invaluable
medicinal
agrochemistry,
natural
products
chemistry
as
well
materials
science.
Over
past
decade,
first-row
d-block
transition
metals
have
increasingly
widely
used
catalysts
for
formation
bond,
traditionally
catalyzed
by
expensive
precious
metals.
This
recent
focus
on
alternative
enabled
growth
fundamental
methods
organoboron
chemistry.
review
surveys
current
state-of-the-art
use
element-based
bonds.
Synthesis,
Год журнала:
2017,
Номер
49(15), С. 3323 - 3336
Опубликована: Июль 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
Angewandte Chemie International Edition,
Год журнала:
2018,
Номер
57(46), С. 15227 - 15231
Опубликована: Сен. 25, 2018
An
efficient
method
for
the
metal-free
deaminative
borylation
of
alkylamines,
using
bis(catecholato)diboron
as
boron
source,
to
directly
synthesize
various
alkyl
potassium
trifluoroborate
salts
is
introduced.
The
key
this
high
reactivity
utilization
pyridinium
salt
activated
with
a
catalytic
amount
bipyridine-type
Lewis
base
promoter.
This
transformation
shows
good
functional-group
compatibility
(e.g.,
it
unimpeded
by
presence
ketone,
indole,
internal
alkene,
or
unactivated
chloride)
and
can
serve
powerful
synthetic
tool
amine
groups
in
complex
compounds.
Mechanistic
experiments
computations
suggest
mechanism
which
B2
cat2
unit
intercepts
an
radical
generated
single-electron
transfer
(SET)
from
boron-based
reductant.
Chemical Society Reviews,
Год журнала:
2021,
Номер
50(23), С. 13129 - 13188
Опубликована: Янв. 1, 2021
We
provide
a
comprehensive
overview
of
transition
metal-catalysed
asymmetric
borylation
processes
to
construct
C–B,
C–C,
and
other
C–heteroatom
bonds
with
considerable
attention
devoted
the
reaction
modes
mechanisms
involved.
Journal of the American Chemical Society,
Год журнала:
2018,
Номер
140(20), С. 6221 - 6225
Опубликована: Май 9, 2018
A
method
for
transition
metal-free
1,2-carboboration
of
unactivated
alkenes
with
bis(catecholato)diboron
as
the
boron
source
in
combination
alkyl
halides
component
is
introduced.
The
three-component
reaction
proceeds
via
a
radical
pathway
on
broad
range
alkenes,
and
products
serve
valuable
synthetic
building
blocks.
Density
functional
theory
calculations
provide
insights
into
mechanism.
Nature Communications,
Год журнала:
2021,
Номер
12(1)
Опубликована: Июль 26, 2021
Abstract
Sulfonium
salts
bearing
a
positively
charged
sulfur
atom
with
three
organic
substituents
have
intrigued
chemists
for
more
than
century
their
unusual
structures
and
high
chemical
reactivity.
These
compounds
are
known
to
undergo
facile
single-electron
reduction
emerge
as
valuable
alternative
source
of
aryl
radicals
synthesis.
However,
the
generation
non-stabilized
alkyl
from
sulfonium
has
been
challenge
several
decades.
Here
we
report
treatment
S
-(alkyl)
thianthrenium
generate
key
intermediates
granting
controlled
selective
outcome
ensuing
reactions
under
mild
photoredox
conditions.
The
value
these
reagents
demonstrated
through
efficient
construction
alkylboronates
other
transformations,
including
heteroarylation,
alkylation,
alkenylation,
alkynylation.
developed
method
is
practical,
provides
opportunity
convert
C–OH
bond
C–B
C–C
bonds.
