Electrochemical Three-Component C–H Functionalization of Indoles with Sodium Bisulfite and Alcohols to Access Indole-Containing Sulfonate Esters
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 4, 2025
Herein,
an
efficient
electrochemical
three-component
C-H
functionalization
of
indoles
with
sodium
bisulfite
and
alcohols
is
described,
providing
a
sustainable
convenient
synthetic
route
for
the
construction
structurally
valuable
indole-containing
sulfonate
esters
in
moderate
to
good
yields.
This
protocol
proceeds
undivided
cell
without
any
metal
catalysts
or
oxidants,
features
broad
substrate
scope,
has
excellent
functional
group
tolerance.
Preliminary
mechanistic
studies
suggest
that
radical-radical
pathway
may
be
involved
this
reaction
system.
Язык: Английский
Multicomponent Electrosynthesis of Enaminyl Sulfonates Starting from Alkylamines, SO2, and Alcohols
Florian A. Breitschaft,
Alicia L. Saak,
Christian Krumbiegel
и другие.
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 27, 2025
An
electrochemical
one-pot
synthesis
of
enaminyl
sulfonate
esters
was
established,
featuring
a
quasidivided
cell
under
constant
current
conditions.
The
multicomponent
reaction
utilizes
simple
and
readily
available
alkylamines
an
easy-to-use
stock
solution
SO2
alcohols.
Omission
additional
supporting
electrolyte
through
in-situ-generated
monoalkylsulfite
facilitates
the
downstream
processing.
A
diverse
scope
with
more
than
28
examples
yields
up
to
85%
as
well
20-fold
scale-up
prove
feasibility
this
novel
protocol.
Язык: Английский
Electrochemical strategies for NaX-mediated hydrolysis and alcoholysis of hydrosilanes under mild conditions
Green Chemistry,
Год журнала:
2024,
Номер
26(10), С. 5838 - 5844
Опубликована: Янв. 1, 2024
Electrochemical
approaches
for
NaCl-mediated
hydrolysis
and
NaBr-promoted
alcoholysis
of
hydrosilanes
have
been
well
established
with
satisfied
yields
under
mild
conditions.
Язык: Английский
Automated Optimization of the Synthesis of Alkyl Arenesulfonates in an Undivided Electrochemical Flow Cell
ChemElectroChem,
Год журнала:
2024,
Номер
unknown
Опубликована: Авг. 19, 2024
Abstract
The
necessary
separation
of
anodic
and
cathodic
compartments
in
the
electrochemical
multicomponent
synthesis
alkyl
arenesulfonates
batch
was
overcome
by
transfer
this
reaction
an
undivided
flow
cell.
yield
increased
from
initial
23
%
to
67
optimization
using
Design
Experiments
(DoE).
experiments
were
carried
out
automated
experimental
electrolysis
setup
controlled
automation
software
LABS
(
Laboratory
Automation
Batch
Scheduling
),
open‐source
that
allows
plan
conduct
with
arbitrary,
freely
selectable
setup.
turned
be
stable
provides
reproducible
results.
In
total,
6
examples
are
demonstrated
isolated
yields
up
81
%.
addition,
robust
scalability
a
10‐fold
scale‐up.
Язык: Английский
Electrochemical Synthesis of Alkenylsulfonates from Alkynes, NaHSO3 and Alcohols
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 7, 2024
Comprehensive
Summary
Alkenylsulfonates
are
commonly
encountered
in
medicinal
chemistry,
polymer
and
organic
synthesis.
In
this
research,
an
electrochemical
reaction
involving
alkynes,
NaHSO
3
,
alcohols
has
been
developed.
This
method
yields
functionalized
alkenylsulfonates
good
with
broad
functional
group
tolerance.
Mechanism
studies
indicate
that
anodic
oxidation
of
inorganic
sulfite,
radical
insertion
process,
HAT
process
involved
transformation.
Язык: Английский
Substrate-Controlled Electrochemical Reaction of 2-Alkynylbenzamides, Inorganic Sulfites, and Alcohols
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(22), С. 16873 - 16882
Опубликована: Ноя. 6, 2024
Isoindolones
constitute
a
dominant
structural
class
in
synthetic
and
medicinal
chemistry.
In
this
research,
an
electrochemical
reaction
involving
2-alkynylbenzamides,
inorganic
sulfites,
alcohols
was
first
established
to
provide
sulfonyl
ester-substituted
3-hydroxyisoindolinone
derivatives
moderate
good
yields
with
excellent
functional
group
tolerance.
When
bulky
aryl-substituted
2-alkynylbenzamides
are
utilized
as
substrates,
3-alkylideneisoindolinones
can
be
selectively
generated
chemoselectivity.
Alkoxysulfonyl
radicals
derived
from
the
anodic
oxidation
of
sulfite
involved
transformation.
Язык: Английский
Electrochemical Sulfonylation of Indoles with Inorganic Sulfites and Alcohols: Direct Synthesis of Indole Sulfonic Esters
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 5, 2024
A
direct
electrochemical
sulfonylation
between
indoles,
inorganic
sulfites,
and
alcohols
was
developed,
in
which
various
indoyl
sulfonate
esters
were
prepared
efficiently.
In
this
transformation,
the
easy-handle
cost-effective
sulfite
disclosed
to
engage
a
Csp2–H
as
SO2
source
an
undivided
electrolysis
cell
under
mild
conditions.
addition,
unexpected
paired
electrosynthesis
has
been
achieved,
owing
dual
role
of
led
sulfonylation/reduction
sequence
rapidly
deliver
hydroxyl
substituted
indole
esters.
Язык: Английский