Diborodichloromethane as Versatile Reagent for Chemodivergent Synthesis of gem‐Diborylalkanes
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
63(3)
Опубликована: Дек. 8, 2023
Abstract
The
development
of
boron
reagents
is
crucial
for
synthetic
chemistry.
Herein,
we
present
a
scalable
and
practical
synthesis
diborodichloromethane
(DBDCM)
through
the
reaction
trichloromethyllithium
with
bis(pinacolato)diboron
(B
2
pin
).
resulting
DBDCM
reagent
serves
as
basic
unit
construction
various
structurally
diverse
gem
‐diborylalkanes
controllable
C−Cl
functionalizations.
Moreover,
have
developed
consecutive
tetra‐functionalizations
tertiary
quaternary
carbon
containing
molecules.
use
isotopically
enriched
13
C‐chloroform
10
B
enables
C‐DBDCM
B‐DBDCM
reagents,
which
are
beneficial
convenient
carbon‐13
boron‐10
Язык: Английский
Synthesis of substituted benzylboronates by light promoted homologation of boronic acids with N-sulfonylhydrazones
Chemical Science,
Год журнала:
2023,
Номер
14(47), С. 13765 - 13775
Опубликована: Янв. 1, 2023
The
homologation
of
boronic
acids
with
diazoalkanes
obtained
by
photochemical
decomposition
N
-tosylhydrazones
leads
to
substituted
benzylboronates,
previously
unavailable
under
thermal
conditions.
Batch
and
continuous
flow
reactions
are
described.
Язык: Английский
Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes
Yu-Wen Sun,
Jingkun Zhao,
Xinyu Yan
и другие.
Nature Communications,
Год журнала:
2024,
Номер
15(1)
Опубликована: Дек. 30, 2024
The
strain-release-driven
reactions
of
bicyclo[1.1.0]butanes
(BCBs)
have
received
significant
attention
from
chemists.
Notably,
1,2-migratory
enabled
by
BCB-derived
B-ate
complexes
effectively
complement
the
initiated
common
BCBs.
desired
products
are
particularly
valuable
for
late-stage
transformations
due
to
presence
C-B
bond.
However,
asymmetric
mediated
boronate
progressed
slowly.
In
this
study,
we
develop
an
synthesis
atropisomers
featuring
cis-cyclobutane
boronic
esters
facilitated
1,2-carbon
or
boron
migration
ring-strained
complexes,
achieving
high
enantioselectivity.
reaction
is
compatible
with
various
aryl,
alkenyl,
alkyl
and
B
Язык: Английский
Transition metal-catalyzed reactivity of carbenes with boronic acid derivatives for arylation (alkylation) and beyond
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(35), С. 7062 - 7078
Опубликована: Янв. 1, 2023
This
review
summarizes
the
transition
metal-catalyzed
reactivity
of
carbenes
with
different
boronic
acids
and
esters
to
form
carbon–carbon
bonds,
carbon–boron
beyond.
Язык: Английский
Synthesis of substituted benzylboronates by light promoted homologation of boronic acids with N-sulfonylhydrazones
Опубликована: Сен. 12, 2023
The
synthesis
of
benzylboronates
by
photochemical
homologation
boronic
acids
with
N-sulfonylhydrazones
under
basic
conditions
is
described.
reaction
involves
the
photolysis
N-tosylhydrazone
salt
to
give
a
diazoalkane
followed
geminal
carboborylation
diazoalkane.
Under
mild
conditions,
protodeboronation
unstable
benzylboronic
acid
circumvented
and
pinacolboronates
can
be
isolated
after
pinacol.
metholodogy
has
been
applied
reactions
alkylboronic
N-tosylhydrazones
aromatic
aldehydes
ketones,
arylboronic
aliphatic
ketones.
Moreover,
employment
DBU/DIPEA
bases
combination
allows
for
homogeneous
which
have
adapted
continuous
flow
conditions.
Additionally,
synthetic
versatility
boronates
enables
their
further
transformation
via
Csp3-C
or
Csp3-X
bond
forming
converting
this
methodology
into
novel
method
difunctionalization
carbonyls
N-tosylhydrazones.
Язык: Английский
Synthesis of Carboxylic Acids Containing α-All-Carbon Quaternary Centers from Diazo Compounds and Trialkylboranes
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 26, 2024
The
construction
of
C–C
bonds
to
form
all-carbon
quaternary
centers
remains
a
significant
challenge
in
synthetic
chemistry.
Herein,
we
report
tandem
process
involving
1,2-migration
tetra-coordinated
boron
intermediate
followed
by
Claisen
rearrangement
the
enolate,
achieved
through
reaction
between
allyl
diazoacetates
and
trialkylboranes.
transformation
forms
two
at
carbenic
position
diazo
substrate
single-step
operation
under
neutral
conditions.
Using
this
method,
successfully
realized
gram-scale
formal
total
synthesis
Vincamine,
an
indole
alkaloid
with
pharmacological
activity.
Язык: Английский
Diborodichloromethane as Versatile Reagent for Chemodivergent Synthesis of gem‐Diborylalkanes
Angewandte Chemie,
Год журнала:
2023,
Номер
136(3)
Опубликована: Дек. 8, 2023
Abstract
The
development
of
boron
reagents
is
crucial
for
synthetic
chemistry.
Herein,
we
present
a
scalable
and
practical
synthesis
diborodichloromethane
(DBDCM)
through
the
reaction
trichloromethyllithium
with
bis(pinacolato)diboron
(B
2
pin
).
resulting
DBDCM
reagent
serves
as
basic
unit
construction
various
structurally
diverse
gem
‐diborylalkanes
controllable
C−Cl
functionalizations.
Moreover,
have
developed
consecutive
tetra‐functionalizations
tertiary
quaternary
carbon
containing
molecules.
use
isotopically
enriched
13
C‐chloroform
10
B
enables
C‐DBDCM
B‐DBDCM
reagents,
which
are
beneficial
convenient
carbon‐13
boron‐10
Язык: Английский