European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
27(3)
Опубликована: Ноя. 28, 2023
Abstract
A
visible
light
photoreductive
dearomatizative
alkylation
of
N
‐alkyl
pyridinium
salts
for
producing
4‐alkyl‐1,4‐dihydropyridines
is
described.
The
reaction
harnesses
both
as
the
alkyl
radical
precursors
to
initiate
and
1,4‐dihydropyridin‐4‐yl‐based
alkylating
reagents
terminate
reaction.
In
contrast
reported
electroreductive
procedure
via
key
dihydropyridine
intermediates,
mechanistic
studies
demonstrate
that
this
proceeds
directly
addition
across
ring
followed
by
single
electron
oxidant
(SEO)
dearomatization.
ACS Catalysis,
Год журнала:
2024,
Номер
14(23), С. 17286 - 17292
Опубликована: Ноя. 8, 2024
Herein,
we
demonstrate
the
ability
of
isonitriles
to
be
used
as
alkyl
radical
precursors
in
a
photoredox-catalyzed
transformation
involving
selective
C-N
cleavage
and
Csp
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(20), С. 5685 - 5694
Опубликована: Янв. 1, 2024
The
first
allenylic
alkylation
with
non-activated
aliphatic
amine
derivatives,
Katritzky
salts,
has
been
developed
via
photoredox/nickel
dual-catalyzed
reductive
deaminative
cross-electrophile
coupling.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(13), С. 3557 - 3561
Опубликована: Янв. 1, 2024
Different
allylbenzyl
derivatives
are
synthesized
by
Co-catalyzed
reductive
cross-coupling
from
functionalized
benzyl
Katritzky
pyridinium
salts
and
various
allylic
acetates,
ethers
or
carbonates
in
moderate
to
good
yields
under
mild
conditions.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(37)
Опубликована: Авг. 2, 2024
Abstract
A
strategy
for
transition
metal‐free
cross‐coupling
of
alkyl
nitroso‐carbamates
and
boronic
acids
is
reported.
The
N
‐nitroso
carbamates
are
easily
prepared
from
the
corresponding
amine
in
two
simple
steps.
This
method
allows
synthesis
a
wide
variety
secondary
boronates,
benzylic
boronates
formal
Csp
3
−Csp
2
products
under
operationally
conditions.
Functional
group
tolerance
also
demonstrated
applied
modification
lysine
to
make
non‐canonical
amino
acids.
Faraday Discussions,
Год журнала:
2023,
Номер
247, С. 324 - 332
Опубликована: Янв. 1, 2023
For
primary
and
secondary
alkylpyridinium
salts,
trends
in
ArBr
scope
are
similar,
electrochemical
conditions
compare
well
to
chemical
methods.
Our
study
offers
increased
understanding
the
application
of
deaminative
reductive
cross-couplings.
Angewandte Chemie,
Год журнала:
2024,
Номер
136(37)
Опубликована: Авг. 2, 2024
Abstract
A
strategy
for
transition
metal‐free
cross‐coupling
of
alkyl
nitroso‐carbamates
and
boronic
acids
is
reported.
The
N
‐nitroso
carbamates
are
easily
prepared
from
the
corresponding
amine
in
two
simple
steps.
This
method
allows
synthesis
a
wide
variety
secondary
boronates,
benzylic
boronates
formal
Csp
3
−Csp
2
products
under
operationally
conditions.
Functional
group
tolerance
also
demonstrated
applied
modification
lysine
to
make
non‐canonical
amino
acids.
Angewandte Chemie,
Год журнала:
2024,
Номер
137(1)
Опубликована: Окт. 9, 2024
Abstract
Etherification
and
amination
of
aryl
halide
scaffolds
are
commonly
used
reactions
in
parallel
medicinal
chemistry
to
rapidly
scan
structure–activity
relationships
with
abundant
building
blocks.
Electrochemical
methods
for
etherification
demonstrate
broad
functional
group
tolerance
extended
nucleophile
scope
compared
traditional
methods.
Nevertheless,
there
is
a
need
robust
scale‐transferable
workflows
electrochemical
compound
library
synthesis.
Herein
we
describe
platform
automated
synthesis
C−X
arylation
(X=NH,
OH)
flow
access
libraries.
A
comprehensive
Design
Experiment
(DoE)
study
identifies
an
optimal
protocol
which
generates
high
yields
across>30
scaffolds,
diverse
amines
(including
electron‐deficient
sulfonamides,
sulfoximines,
amides,
anilines)
alcohols
serine
residues
within
peptides).
Reaction
sequences
on
commercially
available
equipment
generate
libraries
anilines
ethers.
The
unprecedented
application
potentiostatic
alternating
polarity
essential
avoid
accumulating
electrode
passivation.
Moreover,
it
enables
be
performed
air,
without
supporting
electrolyte
reproducibility
over
consecutive
runs.
Our
method
represents
powerful
means
independent
using
electrochemistry.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
27(3)
Опубликована: Ноя. 28, 2023
Abstract
A
visible
light
photoreductive
dearomatizative
alkylation
of
N
‐alkyl
pyridinium
salts
for
producing
4‐alkyl‐1,4‐dihydropyridines
is
described.
The
reaction
harnesses
both
as
the
alkyl
radical
precursors
to
initiate
and
1,4‐dihydropyridin‐4‐yl‐based
alkylating
reagents
terminate
reaction.
In
contrast
reported
electroreductive
procedure
via
key
dihydropyridine
intermediates,
mechanistic
studies
demonstrate
that
this
proceeds
directly
addition
across
ring
followed
by
single
electron
oxidant
(SEO)
dearomatization.
