Decatungstate‐Photocatalyzed Diastereoselective Dearomative Hydroalkylation of Indoles
Emeric Montinho‐Inacio,
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Damien Bouchet,
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Wei‐Yang Ma
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et al.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(22)
Published: April 16, 2024
Abstract
In
this
study,
we
present
an
efficient
and
straightforward
dearomative
hydroalkylation
of
indoles.
By
utilizing
alkanes
or
ethers
as
alkyl
radical
sources
employing
TBADT
a
cost‐effective
photocatalyst
for
direct
hydrogen
atom
transfers
(HAT),
achieved
successful
conversion
these
heterocyclic
derivatives
into
2‐alkylindolines
with
good
to
excellent
yields
high
diastereoselectivity
under
mild
reaction
conditions.
Language: Английский
Photoredox-Neutral Deoxygenative Carboxylation of Acylated Alcohols with Tetrabutylammonium Oxalate
Chen-Wei Xu,
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Si-Yi Yan,
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Hui Xu
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et al.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(16), P. 11967 - 11973
Published: July 26, 2024
Herein,
a
photoredox-neutral
strategy
for
carboxylation
of
acylated
alcohols
via
C(sp3)–O
bond
activation
and
cleavage
with
tetrabutylammonium
oxalate
(TBAO)
as
the
carbonyl
source
reductant
well
promoter
is
described.
Neither
pre-established
CO2
atmosphere
nor
external
electron
donors
are
required
TBAO
crucial
transformation.
Various
primary,
secondary,
tertiary
could
be
smoothly
converted
to
corresponding
aryl
acetic
acids,
which
core
structures
diverse
pharmaceutical
drugs.
Language: Английский
Formate Salts: The Rediscovery of Their Radical Reaction under Light Irradiation Opens New Avenues in Organic Synthesis
Qing Shen,
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Kun Cao,
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Xiaoqing Wen
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et al.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(21), P. 4274 - 4293
Published: Aug. 17, 2024
Abstract
Formates
are
abundantly
available
and
inexpensive
commodity
chemical,
widely
used
in
laboratory
industrial
organic
synthesis.
promising
hydrogen
carrier
green
C1
source,
have
also
been
a
subject
of
research
as
SET
reductants
recent
years.
Compared
to
the
toxic
flammable
gas
carbon
monoxide,
which
serves
formates
easier
handle,
store,
transport,
more
environmentally
friendly.
Therefore,
studies
radical
reactions,
formate
is
not
only
an
ideal
source
carbonyl,
great
significance
synthesize
carboxyl
compounds
with
various
structures,
but
reductant
for
editing
molecules
either
scientific
or
production.
The
activation
conversion
formate,
reductant,
very
challenging
hot
field
Language: Английский
Formate‐Mediated Synthesis of β‐Hydroxysulfides from Olefins and Thiosulfonates via EDA Complex Strategy under Visible Light Irradiation in Air
Qing Shen,
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Xiaoyan Peng,
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Jiahong Sui
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et al.
Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
42(23), P. 3129 - 3134
Published: Aug. 13, 2024
Comprehensive
Summary
A
visible‐light‐induced
and
efficient
one‐pot
synthesis
of
β
‐hydroxysulfides
from
olefins,
thiosulfonates
HCOOCs
using
an
EDA
complex
strategy
under
air
atmosphere
at
room
temperature
has
been
disclosed.
plausible
radical
involved
mechanism
is
proposed.
During
the
reaction
process,
formates
play
a
crucial
role:
first,
as
donors
in
complex;
second,
providers
hydrogen
source;
third,
by
generating
CO
2
•–
to
reduce
peroxide
intermediates,
leading
formation
‐hydroxysulfides.
In
contrast
previously
reported
thiol‐oxygen
co‐oxidation
reactions,
this
simple
sustainable
approach
features
mild
conditions,
operational
simplicity,
odorless
excellent
functional
group
tolerance.
Language: Английский
1‐Methylpyridine‐2(1H)‐thione Photocatalyzed Giese Reaction with N‐Hydroxyphthalimide Esters via Single Electron Transfer
Lanting Li,
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Yuzhuo Wang,
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Li Yuan
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et al.
Chinese Journal of Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 18, 2025
Comprehensive
Summary
We
have
developed
a
series
of
1‐methylpyridine‐2(1
H
)‐thione
(MPT)
analogues
to
be
used
as
organocatalysts.
The
MPT
catalysts
are
easily
prepared
and
bench‐stable.
In
our
previous
work,
we
found
that
the
ground‐state
catalyst
could
act
nucleophile
generate
primary
radicals
via
an
S
N
2
pathway.
However,
this
reaction
was
limited
benzyl
radicals.
Herein,
reported
new
catalytic
property
catalyst.
photoexcited
(
E
(MPT
·+
/MPT*)
=
–1.60
V
vs.
Ag/AgCl
in
MeCN)
reduce
NHPI
esters
through
single
electron
transfer
process.
Various
carbon
radicals,
including
radical,
well
primary,
secondary
tertiary
alkyl
generated
easily.
Notably,
amino
acids,
peptide,
pharmaceuticals,
other
biologically
active
molecules
modified
by
using
methodology
showing
potential
synthetic
utility
method.
Language: Английский
HDAC inhibitor SAHA triggers the production of previously undescribed sesquiterpenes and undergoes biotransformation by the fungus Robillarda sessilis from Verbena officinalis L.
Liangxiu Liao,
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Junguo Huang,
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Zhu Tao
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et al.
Phytochemistry,
Journal Year:
2025,
Volume and Issue:
unknown, P. 114411 - 114411
Published: Jan. 1, 2025
Language: Английский
Visible-Light Photoredox-Catalyzed Carboxylation of Benzylic C(sp3)–O Bonds in Ethers with CO2
Jingwei Yang,
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Chuan‐Kun Ran,
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Wenjing Zhu
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et al.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: June 5, 2025
Although
significant
progress
has
been
made
in
achieving
site-selective
C-O
bond
functionalization
specific
substrates,
the
selective
cleavage
and
of
C(sp3)-O
bonds
ethers
remain
a
fundamental
challenge
synthetic
chemistry.
Herein,
we
present
an
efficient
carboxylation
method
via
photoredox-catalyzed
benzylic
with
carbon
dioxide
(CO2).
Diverse
primary,
secondary,
tertiary
benzyl
undergo
CO2
to
generate
valuable
aryl
acetic
acids,
including
several
drug
molecules.
This
photocatalyzed
reaction
is
operationally
simple
implement
versatile
for
various
ethers,
exhibiting
favorable
compatibility
diverse
functional
groups.
Mechanistic
studies
indicate
that
single
electron
transfer
(SET)
reduction
might
be
key
generating
highly
reactive
radical
anion
intermediate,
which
could
another
SET
process
carbanions
CO2.
Language: Английский
Nucleophilic Organocatalyst for Photochemical Carbon Radical Generation via SN2 Substitution
Yuzhuo Wang,
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Shiwen Fan,
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Xinjun Tang
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(18), P. 4002 - 4007
Published: May 1, 2024
Photochemical
generation
of
radicals
is
a
powerful
way
to
construct
various
molecules.
But
most
these
methods
rely
on
initiators
or
the
redox
properties
radical
precursors.
Herein,
we
report
photochemical
organic
catalyst
that
reacts
with
benzyl
halide
generate
carbon
via
an
SN2
pathway.
This
nucleophilic
can
be
easily
prepared
and
bench-stable.
The
process
does
not
halides,
showing
potential
synthetic
utility.
Control
experiments
UV–vis
spectroscopic
analysis
indicate
substitution
adduct
key
intermediate.
Language: Английский
Photoinduced Radical Approach for Desulfurative Alkylation of Cysteine Derivatives to Make Unnatural Amino Acids
Pei Xu,
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Yiqin Liu,
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Hui-Xian Jiang
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 4, 2024
Unnatural
amino
acids
(UAAs)
are
highly
valuable
molecules
in
organic
synthesis,
pharmaceutical
sciences,
and
material
science.
Herein,
we
present
a
photocatalytic
radical
approach
for
desulfurative
alkylation
of
cysteine
derivatives
with
arenethiol
as
the
hydrogen
atom
transfer
catalyst
making
UAAs
peptides.
The
formate
salt,
acting
donor,
situ
generates
reductive
CO
Language: Английский
Visible-Light-Driven Carboxylative 1,2-Difunctionalization of C═C Bonds with Tetrabutylammonium Oxalate
Sai Wang,
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Pei Xu,
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Zhitao Liu
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et al.
ACS Central Science,
Journal Year:
2024,
Volume and Issue:
11(1), P. 46 - 56
Published: Nov. 15, 2024
Herein,
we
report
a
visible-light-induced
charge-transfer-complex-enabled
dicarboxylation
and
deuterocarboxylation
of
C═C
bonds
with
oxalate
as
masked
CO2
source
under
catalyst-free
conditions.
In
this
reaction,
disclosed
the
first
example
that
tetrabutylammonium
could
be
able
to
aggregate
aryl
substrates
via
π–cation
interactions
form
charge
transfer
complexes,
which
subsequently
triggers
single
electron
from
oxalic
dianion
ammonium
countercation
irradiation
450
nm
bule
LEDs,
releasing
radical
anions.
Diverse
alkenes,
dienes,
trienes,
indoles,
including
challenging
trisubstituted
olefins,
underwent
anti-Markovnikov
high
selectivity
access
valuable
1,2-
1,4-dicarboxylic
acids
well
indoline-derived
diacids
β-deuterocarboxylic
mild
The
in
situ
generated
CO2•–
molecules
anions
both
add
bond
without
assistance
any
photocatalyst
or
additives,
made
reaction
sustainable,
clean,
efficient.
Language: Английский