Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(9), С. 2274 - 2289
Опубликована: Март 10, 2021
Abstract
α‐Monoboryl
anions
show
remarkable
stability
due
to
the
valence
deficiency
of
adjacent
three‐coordinate
boron
center
and
can
be
expressed
as
its
resonance
form,
borata‐alkene
systems
[R
2
B=CH
]
−
.
The
diversity
synthetic
approaches
well
properties
C=B
bond
are
disclosed
in
this
review,
dealing
with
both
electronic
structural
boryl
moieties
involved.
Full
characterization
solid
state
by
X‐ray
diffraction
demonstrated
short
distances
between
B
C,
a
consequence
ylide
character
boron‐stabilized
carbanions.
This
review
includes
collection
C−B
length
11
NMR
data
that
useful
for
diagnostic
evidence
partial
boron‐carbon
double‐bond
character.
Natural
orbital
(NBO)
analysis
on
DFT
computed
structures
also
supports
justifies
reactivity
acting
nucleophilic
synthon
is
unveiled
through
extensive
electrophilic
trapping
examples.
homologation
protocols
diborylmethane,
via
single
carbon
chain
extension,
involves
facile
introduction
C(
sp
3
)−B
bonds,
which
subsequently
transformed
into
functionalized
target
products,
containing
C−O,
C−N
or
C−C
bonds.
magnified
image
Angewandte Chemie International Edition,
Год журнала:
2019,
Номер
58(50), С. 18131 - 18135
Опубликована: Сен. 4, 2019
We
report
the
catalytic
enantioselective
conjugate
addition
of
a
borylalkyl
copper
nucleophile
generated
in
situ
from
1,1-diborylmethane
derivative
to
α,β-unsaturated
diesters.
In
presence
chiral
N-heterocyclic
carbene
(NHC)-copper
catalyst,
this
method
facilitated
incorporation
CH2
Bpin
moiety
at
β-position
diesters
yield
β-chiral
alkyl
boronates
up
86
%
with
high
enantioselectivity.
The
alkylboron
resulting
diester
products
was
converted
into
various
functional
groups
by
organic
transformation
C-B
bond.
Chemistry - A European Journal,
Год журнала:
2019,
Номер
25(34), С. 8013 - 8017
Опубликована: Апрель 24, 2019
Vinyl
epoxides
and
styrene
oxide
can
react
with
diborylmethide
lithium
salts
through
an
exclusive
SN
2
borylmethylation/ring
opening
in
a
regio-
diastereoselective
way,
depending
on
the
nature
of
substrate.
The
ring-opening
protocol
provides
homoallylboronates
that
be
transformed
into
challenging
diastereomeric
bishomoallylic
alicyclic
1,3-diols.
Unprecedented
3-borylated
1,2-oxaborolan-2-ol
products
were
prepared
by
2-methyl-2-vinyloxirane
followed
intramolecular
cyclization.
Organic Letters,
Год журнала:
2020,
Номер
22(16), С. 6376 - 6381
Опубликована: Авг. 5, 2020
Reported
herein
is
a
palladium/copper
cooperative-catalyzed
dicarbofunctionalization
of
alkene-tethered
carbamoyl
chlorides
with
1,1-diborylmethane.
This
cyclization/deborylation
cascade
strategy
allows
for
the
expedient
formation
versatile
borylated
3,3-disubstituted
oxindole
skeleton,
allowing
further
functionalization
via
derivatization
carbon-boron
bond.
Organic Letters,
Год журнала:
2020,
Номер
22(18), С. 7158 - 7163
Опубликована: Сен. 3, 2020
A
palladium/XantPhos-catalyzed
[5
+
2]
annulation
of
VECs
with
electron-deficient
alkenes
having
an
isolated
carbon–carbon
double
bond
has
been
developed
to
afford
spirobarbiturate-tetrahydrooxepines.
This
study
provides
expedient
assembly
biologically
interesting
The
easy
scalability
and
versatile
transformability
the
reaction
products
were
also
exhibited.
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(9), С. 2274 - 2289
Опубликована: Март 10, 2021
Abstract
α‐Monoboryl
anions
show
remarkable
stability
due
to
the
valence
deficiency
of
adjacent
three‐coordinate
boron
center
and
can
be
expressed
as
its
resonance
form,
borata‐alkene
systems
[R
2
B=CH
]
−
.
The
diversity
synthetic
approaches
well
properties
C=B
bond
are
disclosed
in
this
review,
dealing
with
both
electronic
structural
boryl
moieties
involved.
Full
characterization
solid
state
by
X‐ray
diffraction
demonstrated
short
distances
between
B
C,
a
consequence
ylide
character
boron‐stabilized
carbanions.
This
review
includes
collection
C−B
length
11
NMR
data
that
useful
for
diagnostic
evidence
partial
boron‐carbon
double‐bond
character.
Natural
orbital
(NBO)
analysis
on
DFT
computed
structures
also
supports
justifies
reactivity
acting
nucleophilic
synthon
is
unveiled
through
extensive
electrophilic
trapping
examples.
homologation
protocols
diborylmethane,
via
single
carbon
chain
extension,
involves
facile
introduction
C(
sp
3
)−B
bonds,
which
subsequently
transformed
into
functionalized
target
products,
containing
C−O,
C−N
or
C−C
bonds.
magnified
image
