Decarboxylative Alkylation of Morita–Baylis–Hillman Acetates with Aliphatic Acids via Photochemical Iron-Mediated Ligand-to-Metal Charge Transfer
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 28, 2025
Carboxylic
acids
are
bench-stable
and
readily
available
chemical
feedstocks
that
function
as
optimal
fundamental
synthetic
platforms
for
the
construction
of
C(sp3)–C(sp3)
bonds
via
decarboxylation
processes.
We
present
a
novel
practical
protocol
decarboxylative
alkylation
Morita–Baylis–Hillman
acetates
with
various
carboxylic
photoinduced
iron-mediated
ligand-to-metal
charge
transfer
(LMCT)
process
under
redox-neutral
conditions.
This
method
exhibits
remarkable
tolerance
to
wide
array
acids,
including
primary,
secondary,
tertiary
obviating
requirement
preactivated
radical
precursors.
The
preliminary
mechanistic
analyses
indicate
pathway
is
involved
in
this
catalytic
transformation.
Язык: Английский
Direct C–H Alkylation of Benzothiadiazoles via Organic Photoredox Catalysis
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(4), С. 2777 - 2781
Опубликована: Фев. 5, 2024
2,1,3-Benzothiadiazole
is
widely
used
as
a
privileged
scaffold
in
pharmaceuticals
and
organic
functional
materials.
Nonetheless,
many
current
methods
for
the
functionalization
of
2,1,3-benzothiadiazole
rely
on
preactivation,
transition
metal
catalysts/promoters,
or
an
elevated
reaction
temperature.
Herein
we
disclose
transition-metal-free
visible-light-induced
photocatalytic
method
direct
C–H
alkylation
using
readily
accessible
carboxylic
acid
derivatives,
i.e.,
N-hydroxyphthalimide
esters
(NHPEs),
alkylating
reagents
under
room
This
mild
scalable
highlighted
by
late-stage
installation
benzothiadiazole
drugs
natural
products.
Язык: Английский
Visible light-mediated decarboxylative allylic alkylation of Morita–Baylis–Hillman acetates with unactivated aliphatic acids
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
Herein,
a
visible
light-induced
and
metal-free
strategy
for
the
direct
decarboxylative
allylic
alkylation
of
Morita–Baylis–Hillman
acetates
with
aliphatic
acids
under
redox-neutral
conditions
has
been
developed.
Язык: Английский
Photoredox/Nickel-Catalyzed Diastereoselective Allylation of Aldehydes with Morita–Baylis–Hillman Adducts
ACS Catalysis,
Год журнала:
2025,
Номер
unknown, С. 8303 - 8316
Опубликована: Май 2, 2025
Язык: Английский
Electrochemical Stereoselective Synthesis of (Z)‐Allyl Aryl Selenides and Sulfides from Baylis‐Hillman Acetates
Li Sun,
Mengcan Xia,
Guorui Yu
и другие.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(5), С. 1152 - 1157
Опубликована: Янв. 9, 2024
Abstract
This
research
presents
a
method
for
the
oxidative
selenylation
and
thiolylation
of
Morita‐Baylis‐Hillman
adducts
through
constant‐current
electrolysis
in
an
undivided
cell
at
room
temperature.
The
reaction
enables
direct
production
trisubstituted
(
Z
)‐allyl
aryl
selenides
sulfides
with
yields
27–98%.
A
wide
variety
different
functionalities
are
well
tolerated
under
these
conditions.
strategy
could
be
carried
out
on
gram
scale
several
synthetic
transformations
were
accomplished
construction
other
allyl
selenide
derivatives.
Control
experiments
mechanistic
studies
indicate
radical
or
ionic
addition
pathway
this
electrochemical
transformation.
Язык: Английский