A General Three-Component Alkyl Petasis Boron–Mannich Reaction
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(31), С. 21769 - 21777
Опубликована: Июль 29, 2024
Aryl
amines
are
one
of
the
most
common
moieties
in
biologically
active
molecules,
and
approximately
37%
drug
candidates
contain
aromatic
amines.
Recent
advancements
medicinal
chemistry,
coined
"escaping
from
flatland",
have
led
to
a
greater
focus
on
accessing
highly
functionalized
C
(sp3)-rich
improve
physicochemical
pharmacokinetic
properties
compounds.
This
article
presents
modular
operationally
straightforward
three-component
alkyl
Petasis
boron–Mannich
(APBM)
reaction
that
utilizes
ubiquitous
starting
materials,
including
amines,
aldehydes,
boronates.
By
adaptation
this
transformation
high-throughput
experimentation
(HTE),
it
offers
rapid
access
an
array
diverse
C(sp3)-rich
complex
amenable
for
identification
candidates.
Язык: Английский
HighlyE‐Selective Olefin Synthesis Catalysed by Novel Quinoxalinone Photocatalyst under Visible Light Conditions
Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(27)
Опубликована: Фев. 21, 2023
In
photo-induced
olefin
synthesis,
the
photocatalysts
with
high
triplet
energy
could
cause
isomerization
of
olefins.
This
study
demonstrates
a
new
quinoxalinone
photocatalytic
system
for
highly
stereoselective
alkenes
preparation
from
alkenyl
sulfones
and
alkyl
boronic
acids.
Our
photocatalyst
not
convert
thermodynamically
favored
E-olefin
to
Z-olefin,
guaranteeing
E-configuration
selectivity
reaction.
There
is
weak
interaction
between
acids
according
NMR
experiments,
probably
decreasing
oxidation
potential
can
be
further
extended
allyl
alkynyl
give
corresponding
alkynes.
Язык: Английский
Effect of orbital hybridization inspired tessellation strategy on the mechanical properties of lattice structures
Thin-Walled Structures,
Год журнала:
2024,
Номер
205, С. 112396 - 112396
Опубликована: Авг. 31, 2024
Язык: Английский
Bromine Radical Release from Nickel-Complex Facilitates the Activation of Alkyl Boronic Acids: A Boron Selective Suzuki-Miyaura Cross Coupling
Chemical Science,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
The
release
of
bromine
radicals
from
a
nickel
complex
via
homolytic
cleavage
under
visible
light
allows
the
activation
alkyl
boronic
acids,
which
participate
in
Suzuki–Miyaura
cross-coupling
process
batch
and
continuous
flow
settings.
Язык: Английский
Boronic Acids and Their Derivatives as Continuous-Flow-Friendly Alkyl Radical Precursors
Synlett,
Год журнала:
2023,
Номер
34(14), С. 1662 - 1677
Опубликована: Апрель 4, 2023
Abstract
Since
its
recognition
as
an
enabling
tool
to
form
challenging
C–C
and
C–heteroatom
bonds
under
mild
sustainable
conditions,
photoredox
catalysis
has
been
in
the
spotlight
within
synthetic
community.
As
a
consequence,
interest
developing
novel
strategies
spiked
together
with
need
define
suitable
technologies
overcome
scale-up
issues
dictated
by
Bouguer–Beer–Lambert
law.
In
this
context,
continuous-flow
reactors
play
major
role
increasing
efficiency
of
given
photocatalyzed
reaction,
thus
rendering
processes
more
accessible.
alkyl
radical
precursor
landscape,
boron-based
species
have
begun
predominant
role.
Though
reactivity
trifluoroborates
deeply
investigated,
using
other
boron
precursors
reactions
recently
arisen.
This
late
exploration
lies
fact
that
high
oxidation
potential
boronic
acids
(BAs)
hinders
their
possible
applications.
Nevertheless,
circumvent
issue,
diverse
array
activation
modes
developed,
exploiting
most
cases
inherent
Lewis
acidity
acid.
The
aim
Account
is
highlight
our
recent
contribution
vibrant
field
focus
on
broad
applicability,
selectivity,
scalability
via
methodology.
For
sake
clarity,
discussed
following
sections.
1
Introduction
2
Why
Photochemistry
Flow?
2.1
Preliminary
Considerations
2.2
Batch
vs.
Flow
Photochemical
Reactions
2.3
Commercially
Available
Lab-Scale
Solutions
for
Photoflow
Chemistry
3
Organoboron
Compounds
3.1
Evolution
Radical
Precursors
Photoredox
Catalysis
3.2
4
Activation
Boronic
Acids
towards
Formation
4.1
Giese-Type
Addition
4.2
Petasis
Reaction
4.3
Light-Driven
Four-Component
4.4
Minisci
5
Conclusion
Future
Perspective
Язык: Английский
Alkoxide-Assisted Stereoselective Functionalization of 1,2-Bis-boronic Esters Under Photoredox Catalysis
Organic Letters,
Год журнала:
2024,
Номер
26(31), С. 6760 - 6765
Опубликована: Июль 25, 2024
Site-specific
functionalization
of
the
secondary
C–B
bond
1,2-bis-boronic
esters
has
been
proven
to
be
an
important
method
for
generation
1,2-bis-functionalized
compounds
in
a
highly
stereoselective
manner.
We
have
explored
previously
unknown
selective
alkenylation,
allylation,
alkynylation
and
addition
aryl
vinyl
trifluoromethane,
which
proceeds
via
novel
reaction
mechanism:
alkoxide-mediated
photoredox
activation
generate
radicals
over
primary
one.
Язык: Английский
A Pd-catalyzed organometallic-free homologation of arylboronic acids enabled by chemoselective transmetalation
Опубликована: Фев. 28, 2023
A
Pd-catalyzed
homologation
of
arylboronic
acids
is
reported.
Halomethylboronic
acid
pinacol
esters
(BPin)
undergo
a
remarkably
facile,
yet
rare,
oxidative
addition
enabled
by
an
alpha-boryl
effect.
Simultaneous
chemoselective
transmetalation
allows
use
these
reagents
for
formal
C1
insertion
to
deliver
benzyl
BPin
products
without
the
requirement
stoichiometric
organometallic
reagents.
The
utility
process
demonstrated
stepwise
C(sp3)C(sp2)
cross-coupling
boronic
ester
into
diarylmethane
pharmacophores
and
electrophile/nucleophile
cross-coupling.
Control
exper-iments
that
demonstrate
reactivity
enhancement
provided
-boryl
effect
are
provided,
along
with
description
limitations
process.
Язык: Английский