Visible-Light-Induced Synthesis of Esters via a Self-Propagating Radical Reaction
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
90(4), С. 1616 - 1627
Опубликована: Янв. 16, 2025
We
herein
disclose
a
visible-light-induced
synthesis
of
O-aryl
esters
through
the
cross-dehydrogenative
coupling
aldehydes
with
phenols
using
BrCCl3,
in
which
phenolate
functions
as
both
substrate
and
photosensitizer.
This
transition-metal-
photocatalyst-free
esterification
is
suitable
for
wide
range
substrates
gives
moderate
to
excellent
yields
(up
95%).
Mechanistic
studies
provided
evidence
self-propagating
radical
reaction
involving
homolytic
cleavage
aldehydic
C–H
bond
formation
acyl
bromides.
BrCCl3
serves
an
oxidant
hydrogen
atom
transfer
(HAT)
agent.
Язык: Английский
Novel Azo dyes containing a hydrazide-hydrazone moiety for dyeing polyester fabric
Scientific Reports,
Год журнала:
2025,
Номер
15(1)
Опубликована: Фев. 5, 2025
Язык: Английский
Late-Stage Radical C–H Alkylamination of Tyrosine Compounds and Phenol-Containing Drugs
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 3, 2024
A
modular
site-selective
iron-catalyzed
radical
amination
of
a
number
phenol-containing
biomolecules
such
as
tyrosine-containing
peptides,
estrogens,
and
other
phenol-based
pharmaceuticals
has
been
developed.
The
method
features
the
use
cost-efficient
combination
FeBr
Язык: Английский
C–H acylation as an enabling tool to tag phenolic drugs
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
A
Pd-catalyzed
directed
C–H
acylation
of
a
collection
intricate
phenol-containing
compounds
with
ethanol
and
other
alcohols
aldehydes
is
reported.
Язык: Английский
Biocatalytic Formal Asymmetric para-Aminoethylation of Unprotected Phenols to Chiral Amines
ACS Catalysis,
Год журнала:
2024,
Номер
15(1), С. 81 - 90
Опубликована: Дек. 13, 2024
Enantiomerically
pure
amines
are
vital
for
the
development
of
biologically
active
compounds
in
medicine
and
agriculture.
While
aminoalkylation
phenols
is
well-established
creating
nitrogen-containing
frameworks,
regio-
stereoselective
para-aminoethylation
unprotected
underexplored.
To
fill
this
gap,
we
propose
a
one-pot
cascade
biocatalysis
system
asymmetric
into
chiral
amines,
using
simple
pyruvate,
NH4Cl,
D/l-alanine
as
starting
materials.
Utilizing
modular
approach,
successfully
performed
through
sequential
process
vinylation
hydroamination,
achieving
good
conversions
(51.0–72.0%)
>99%
ee
both
enantiomers
amines.
Additionally,
biobased
p-hydroxycinnamic
acid
l-tyrosine
their
derivatives
were
converted
with
moderate
to
(39.4–87%)
integrating
decarboxylation/hydroamination
deamination-decarboxylation/hydroamination.
This
marks
successful
de
novo
biosynthesis
method
formal
phenols.
Язык: Английский
Cesium and Phenoxide Interaction Enabled by Rh Overrides the Innate Solvent-Mediated Chemoselectivity
ACS Catalysis,
Год журнала:
2024,
Номер
14(16), С. 12351 - 12358
Опубликована: Авг. 5, 2024
DLPNO-CCSD(T)
calculations
are
carried
out
to
understand
the
distinctive
chemoselectivity
in
a
Rh(II)-catalyzed
carbene
insertion
into
C(sp2)–H
bond
unprotected
phenols
without
preinstalled
directing
groups.
As
per
conventional
rules
of
solvation
and
separated
ion
pair
polar
aprotic
solvents
like
acetonitrile,
reaction
should
have
resulted
an
O–H
insertion.
However,
our
reveal
transition
state
model
that
helps
overriding
innate
acetonitrile.
It
involves
explicit
participation
added
Cs2CO3
base,
where
interaction
between
phenoxide
oxygen
Cs
cation,
but
not
as
metal-bound
phenoxide,
is
crucial
for
controlling
chemoselectivity.
Our
study
will
be
helpful
developing
further
reactions
with
broad
catalyst,
substrate,
solvent
scope.
Язык: Английский