Journal of the American Chemical Society,
Journal Year:
2022,
Volume and Issue:
144(14), P. 6442 - 6452
Published: April 1, 2022
The
enantioconvergent
radical
C(sp3)–C(sp2)
cross-coupling
of
alkyl
halides
with
alkenylboronate
esters
is
an
appealing
tool
in
the
assembly
synthetically
valuable
enantioenriched
alkenes
owing
to
ready
availability,
low
toxicity,
and
air/moisture
stability
esters.
Here,
we
report
a
copper/chiral
N,N,N-ligand
catalytic
system
for
benzyl/propargyl
(>80
examples)
good
functional
group
tolerance.
key
success
rational
design
hemilabile
N,N,N-ligands
by
mounting
steric
hindrance
at
ortho
position
one
coordinating
quinoline
ring.
Thus,
newly
designed
ligand
could
not
only
promote
process
tridentate
form
but
also
deliver
enantiocontrol
over
highly
reactive
radicals
bidentate
form.
Facile
follow-up
transformations
highlight
its
potential
utility
synthesis
various
building
blocks
as
well
late-stage
functionalization
drug
discovery.
Chemical Reviews,
Journal Year:
2021,
Volume and Issue:
121(7), P. 3561 - 3597
Published: Feb. 17, 2021
Organoboron
compounds
have
important
synthetic
value
and
can
be
applied
in
numerous
transformations.
The
development
of
practical
convenient
ways
to
synthesize
boronate
esters
has
thus
attracted
significant
interest.
Photoinduced
borylations
originated
from
stoichiometric
reactions
alkanes
arenes
with
well-defined
metal–boryl
complexes.
Now,
photoredox-initiated
borylations,
catalyzed
by
either
transition
metal
or
organic
photocatalysts,
photochemical
high
efficiency
become
a
burgeoning
area
research.
In
this
Focus
Review,
we
summarize
research
on
photoinduced
especially
emphasizing
recent
developments
trends.
This
includes
the
borylation
arenes,
alkanes,
aryl/alkyl
halides,
activated
carboxylic
acids,
amines,
alcohols,
so
based
catalysis,
metal-free
organocatalysis,
direct
activation.
We
focus
reaction
mechanisms
involving
single-electron
transfer,
triplet-energy
other
radical
processes.
Chemical Reviews,
Journal Year:
2021,
Volume and Issue:
121(21), P. 13238 - 13341
Published: Oct. 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.
Journal of the American Chemical Society,
Journal Year:
2019,
Volume and Issue:
141(51), P. 20069 - 20078
Published: Dec. 13, 2019
An
intermolecular,
photocatalytic
dicarbofunctionalization
(DCF)
of
olefins
enabled
by
the
merger
Giese-type
addition
with
Ni/photoredox
dual
catalysis
has
been
realized.
Capitalizing
on
rapid
3°
radicals
to
alkenes
and
their
reluctance
toward
single
electron
metalation
Ni
complexes,
regioselective
alkylation
arylation
is
possible.
This
catalytic
method
not
only
permits
elaborate
species
be
assembled
from
commodity
materials,
but
also
allows
quaternary
tertiary
centers
installed
in
a
singular,
chemoselective
olefin
difunctionalization.
multicomponent
process
occurs
under
exceptionally
mild
conditions,
compatible
diverse
range
functional
groups
synthetic
handles
such
as
pinacolboronate
esters.
technology
was
directly
applied
synthesis
an
intermediate
preclinical
candidate
(TK-666)
its
derivatives.
Chemical Society Reviews,
Journal Year:
2022,
Volume and Issue:
51(21), P. 8877 - 8922
Published: Jan. 1, 2022
This
review
covers
the
development
of
transition
metal-catalysed
hydroboration
reaction,
from
its
beginnings
in
1980s
to
more
recent
developments
including
earth-abundant
catalysts
and
an
ever-expanding
array
substrates.
Chemical Reviews,
Journal Year:
2022,
Volume and Issue:
122(6), P. 6749 - 6794
Published: Feb. 24, 2022
Dipolar
aprotic
and
ethereal
solvents
comprise
just
over
40%
of
all
organic
utilized
in
synthetic
organic,
medicinal,
process
chemistry.
Unfortunately,
many
the
common
"go-to"
are
considered
to
be
"less-preferable"
for
a
number
environmental,
health,
safety
(EHS)
reasons
such
as
toxicity,
mutagenicity,
carcinogenicity,
or
practical
handling
flammability
volatility.
Recent
legislative
changes
have
initiated
implementation
restrictions
on
use
commonly
employed
dipolar
dimethylformamide
(DMF)
N-methyl-2-pyrrolidinone
(NMP),
ethers
1,4-dioxane.
Thus,
with
growing
legislative,
EHS,
societal
pressures,
need
identify
implement
alternative
that
greener,
safer,
more
sustainable
has
never
been
greater.
Within
this
review,
ubiquitous
nature
is
discussed
respect
physicochemical
properties
made
them
so
appealing
chemists.
An
overview
current
being
imposed
discussed.
A
variety
alternative,
garnered
attention
past
decade
then
examined,
case
studies
examples
where
less-preferable
successfully
replaced
safer
highlighted.
Finally,
general
guidance
solvent
selection
replacement
included
Supporting
Information
review.
Chemical Society Reviews,
Journal Year:
2023,
Volume and Issue:
52(9), P. 2946 - 2991
Published: Jan. 1, 2023
This
review
discusses
the
applications
of
N-heterocyclic
carbene
ligands
and
their
influence
on
reactivity
selectivity
Ni-catalysed
alkene
functionalisations.
