Nature Communications,
Journal Year:
2021,
Volume and Issue:
12(1)
Published: Nov. 19, 2021
Electrosynthesis
has
received
great
attention
among
researchers
in
both
academia
and
industry
as
an
ideal
technique
to
promote
single
electron
reduction
without
the
use
of
expensive
catalysts.
In
this
work,
we
report
electrochemical
Katritzky
salts
alkyl
radicals
by
sacrificing
easily
accessible
metal
anode.
This
catalyst
electrolyte
free
platform
broad
applicability
transfer
chemistry,
including
fluoroalkenylation,
alkynylation
thiolation.
The
deaminative
functionalization
is
facilitated
rapid
molecular
diffusion
across
microfluidic
channels,
demonstrating
practicality
that
outpaces
conventional
electrochemistry
setups.
Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
59(16), P. 6513 - 6519
Published: Feb. 4, 2020
The
first
electrochemical
approach
for
nickel-catalyzed
cross-electrophile
coupling
was
developed.
This
method
provides
a
novel
route
to
1,1-diarylalkane
derivatives
from
simple
and
readily
available
alkyl
aryl
halides
in
good
yields
excellent
regioselectivity
under
mild
conditions.
procedure
shows
tolerance
broad
variety
of
functional
groups
both
primary
secondary
can
be
used.
Furthermore,
the
reaction
successfully
scaled
up
multigram
scale,
thus
indicating
potential
industrial
application.
Mechanistic
investigation
suggested
formation
nickel
hydride
electroreductive
chain-walking
arylation,
which
led
development
new
hydroarylation
styrenes
provide
series
1,1-diaryl
alkanes
Green Chemistry,
Journal Year:
2020,
Volume and Issue:
22(21), P. 7301 - 7320
Published: Jan. 1, 2020
This
review
discusses
recent
advances
in
the
photocatalytic
carboxylation
of
C(sp3)–X
(X
=
H,
N)
bonds,
C(sp2)–X
N,
(pseudo)halide)
bonds
and
C(sp)–H
with
CO2.
Chemical Society Reviews,
Journal Year:
2021,
Volume and Issue:
50(16), P. 8903 - 8953
Published: Jan. 1, 2021
The
formation
of
C–aryl
bonds
has
been
the
focus
intensive
research
over
last
decades
for
construction
complex
molecules
from
simple,
readily
available
feedstocks.
Journal of the American Chemical Society,
Journal Year:
2022,
Volume and Issue:
144(3), P. 1130 - 1137
Published: Jan. 14, 2022
Herein,
we
report
the
first
Ni-catalyzed
enantioselective
deaminative
alkylation
of
amino
acid
and
peptide
derivatives
with
unactivated
olefins.
Key
for
success
was
discovery
a
new
sterically
encumbered
bis(oxazoline)
ligand
backbone,
thus
offering
de
novo
technology
accessing
enantioenriched
sp3–sp3
linkages
via
sp3
C–N
functionalization.
Our
protocol
is
distinguished
by
its
broad
scope
generality
across
wide
number
counterparts,
even
in
context
late-stage
In
addition,
an
remote
hydroalkylation
reaction
internal
olefins
within
reach,
providing
useful
entry
point
forging
centers
at
C–H
sites.
Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(10), P. 5684 - 5695
Published: Feb. 28, 2023
A
deaminative
reductive
coupling
of
amino
acid
pyridinium
salts
with
aryl
bromides
has
been
developed
to
enable
efficient
synthesis
noncanonical
acids
and
diversification
peptides.
This
method
transforms
natural,
commercially
available
lysine,
ornithine,
diaminobutanoic
acid,
diaminopropanoic
alanines
homologated
derivatives
varying
chain
lengths.
Attractive
features
include
ability
transverse
scales,
tolerance
pharma-relevant
(hetero)aryls
biorthogonal
functional
groups,
the
applicability
beyond
monomeric
short
macrocyclic
peptide
substrates.
The
success
this
work
relied
on
high-throughput
experimentation
identify
complementary
reaction
conditions
that
proved
critical
for
achieving
a
broad
scope
range
substrates
including
Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
59(32), P. 13484 - 13489
Published: May 6, 2020
Abstract
While
ketones
are
among
the
most
versatile
functional
groups,
their
synthesis
remains
reliant
upon
reactive
and
low‐abundance
starting
materials.
In
contrast,
amide
formation
is
most‐used
bond‐construction
method
in
medicinal
chemistry
because
reliable
draws
large
diverse
substrate
pools.
A
new
for
of
presented
here
that
from
same
substrates
used
bond
synthesis:
amines
carboxylic
acids.
nickel
terpyridine
catalyst
couples
N‐alkyl
pyridinium
salts
with
situ
formed
acid
fluorides
or
2‐pyridyl
esters
under
reducing
conditions
(Mn
metal).
The
reaction
has
a
broad
scope,
as
demonstrated
by
35
different
bearing
wide
variety
groups
an
average
yield
60±16
%.
This
approach
capable
coupling
substrates,
including
pharmaceutical
intermediates,
to
rapidly
form
complex
ketones.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(8), P. 2947 - 2951
Published: March 29, 2019
A
Ni-catalyzed
reductive
deaminative
arylation
at
unactivated
sp3
carbon
centers
is
described.
This
operationally
simple
and
user-friendly
protocol
exhibits
excellent
chemoselectivity
profile
broad
substrate
scope,
thus
complementing
existing
metal-catalyzed
cross-coupling
reactions
to
forge
C–C
linkages.
These
virtues
have
been
assessed
in
the
context
of
late-stage
functionalization,
hence
providing
a
strategic
advantage
reliably
generate
structure
diversity
with
amine-containing
drugs.
Advanced Synthesis & Catalysis,
Journal Year:
2019,
Volume and Issue:
361(19), P. 4500 - 4505
Published: Aug. 6, 2019
Abstract
We
report
herein
a
catalyst‐free
method
to
perform
decarboxylative
conjugated
addition
and
hydrodecarboxylation
of
aliphatic
N‐(acyloxy)phthalimides
(redox
active
esters,
RAEs)
through
photoactivation
electron‐donor‐acceptor
(EDA)
complex
with
Hantzsch
ester
(HE)
in
N,N‐dimethylacetamide
(DMA)
solution.
The
reactions
present
green
decarboxylatively
construct
carbon‐carbon
bond
broad
substrate
scope
functional
group
tolerance
under
mild
blue
light
irradiation
condition
without
recourse
popularly
used
photoredox
catalysts.
magnified
image
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(21), P. 8673 - 8678
Published: Oct. 22, 2019
A
visible-light-mediated
deaminative
thioesterification
of
amino
acid
derived
Katritzky
salts
with
thiobenzoic
has
been
developed,
which
provides
a
novel
synthetic
method
for
the
synthesis
α-mercapto
derivatives
under
mild
conditions.
This
photoredox
catalyst-free
generation
alkyl
radicals
via
C-N
bond
cleavage
is
enabled
by
formation
an
electron-donor-acceptor
(EDA)
complex
between
salt
and
anion,
represents
new
entry
EDA
chemistry.
