Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
365(1), P. 23 - 30
Published: Dec. 20, 2022
Abstract
We
developed
a
cost‐effective
cobalt‐catalyzed
electrochemical
annulation
to
generate
diversified
novel
complex
dihydroisoquinolin
derivatives
from
amides
and
alkenes
in
simple
maneuverable
undivided
cell.
The
reaction
proceeded
C−H/N−H
activation,
the
catalyst
was
regenerated
by
anodic
oxidation.
Notably,
strategy
of
electrocatalysis
avoided
consumption
stoichiometric
chemical
oxidants.
magnified
image
Chemical Reviews,
Journal Year:
2023,
Volume and Issue:
123(19), P. 11269 - 11335
Published: Sept. 26, 2023
Late-stage
functionalization
(LSF)
constitutes
a
powerful
strategy
for
the
assembly
or
diversification
of
novel
molecular
entities
with
improved
physicochemical
biological
activities.
LSF
can
thus
greatly
accelerate
development
medicinally
relevant
compounds,
crop
protecting
agents,
and
functional
materials.
Electrochemical
synthesis
has
emerged
as
an
environmentally
friendly
platform
transformation
organic
compounds.
Over
past
decade,
electrochemical
late-stage
(eLSF)
gained
major
momentum,
which
is
summarized
herein
up
to
February
2023.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(4), P. 990 - 995
Published: Jan. 1, 2023
A
site-selective
electrochemical
C–H
bromination
of
(hetero)arenes
with
2-bromoethan-1-ol
by
releasing
available
ethylene
oxide
and
hydrogen
through
paired
electrolysis
has
been
developed.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(20)
Published: Feb. 24, 2023
Glycosyl
anomeric
radical
addition
reactions
have
been
well-explored
and
proved
efficient
for
the
C-alkyl
glycosides
synthesis,
but
multicomponent
Domino
transformations
rapid
controllable
construction
of
structurally
diversified
in
a
single
step
are
still
rare.
In
contrast,
we,
herein,
report
ruthenium(II)-catalyzed
meta-C-H
ethyl
glycosylation,
enabling
challenging
meta-C-alkyl
glycosides.
Our
ruthenium(II)
catalysis
was
reflected
by
mild
reaction
condition,
exclusive
meta-site
selectivity
high
levels
selectivity.
addition,
glycosylation
allowed
synthesis
versatile
1,2-trans-C-alkyl
with
commercially
available
vinyl
arenes,
acrylates
easily
accessible
glycosyl
bromides.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(20)
Published: Feb. 16, 2022
While
electrochemical
ortho-selective
C-H
activations
are
well
established,
distal
continue
to
be
underdeveloped.
In
contrast,
we
herein
describe
the
meta-C-H
functionalization.
The
remote
bromination
was
accomplished
in
an
undivided
cell
by
RuCl
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(42)
Published: July 25, 2022
Abstract
The
prevalence
of
C
‐aryl
glycosides
in
biologically
active
natural
products
and
approved
drugs
has
long
motivated
the
development
efficient
strategies
for
their
selective
synthesis.
Cross‐couplings
have
been
frequently
used,
but
largely
relied
on
palladium
catalyst
with
prefunctionalized
substrates,
while
ruthenium‐catalyzed
glycoside
preparation
thus
far
proven
elusive.
Herein,
we
disclose
a
versatile
ruthenium(II)‐catalyzed
meta
‐C−H
glycosylation
to
access
‐
from
readily
available
glycosyl
halide
donors.
robustness
ruthenium
catalysis
was
reflected
by
mild
reaction
conditions,
outstanding
levels
anomeric
selectivity
exclusive
‐site‐selectivity.
Chemical Society Reviews,
Journal Year:
2023,
Volume and Issue:
52(18), P. 6359 - 6378
Published: Jan. 1, 2023
This
review
discusses
the
important
role
of
silver(
i
)
salts
as
additives
in
transition-metal
catalyzed
C–H
activation,
and
depicts
discussion
about
current
shift
towards
Ag-free
procedures,
plausible
sustainable
alternatives.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(11), P. 8160 - 8167
Published: May 10, 2024
Rhodium(III)-catalyzed
enantioselective
C–H
activation
has
emerged
as
a
powerful
tool
for
assembling
enabling
chiral
molecules.
However,
this
approach
is
significantly
hampered
by
the
cumbersome
synthetic
routes
preparing
rhodium
catalysts.
In
sharp
contrast,
we
herein
report
on
an
electrochemical
domino
catalysis
system
that
exploits
achiral
Cp*-rhodium
catalyst
along
with
easily
accessible
Brønsted
base
activation/annulation
reaction
of
alkenes
benzoic
acids.
Our
strategy
offers
environmentally
benign
and
most
user-friendly
synthetically
useful
phthalides
in
good
enantioselectivity,
employing
electricity
sustainable
oxidant.
ACS Catalysis,
Journal Year:
2022,
Volume and Issue:
12(18), P. 11089 - 11096
Published: Aug. 26, 2022
Aryl
halides
are
important
chemical
components
in
organic
syntheses.
Herein,
we
report
visible-light-induced,
single
nickel-catalyzed
halogen
exchange
of
aromatic
with
the
corresponding
halide
salts
under
mild
conditions.
Varieties
aryl
iodides,
bromides,
and
chlorides
can
smoothly
undergo
Finkelstein
or
retro-Finkelstein
reactions
good
functional
group
tolerance.
Experimentally,
mechanistic
studies
showed
that
excited-state
NiII
complexes
for
facile
reductive
elimination
to
form
carbon–halide
bonds
were
involved
process
reactions.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(22)
Published: Feb. 27, 2023
Ruthenium-catalyzed
σ-bond
activation-assisted
meta-C-H
functionalization
has
emerged
as
a
useful
tool
to
forge
distal
C-C
bonds.
However,
given
the
limited
number
of
mechanistic
studies,
clear
understanding
origin
site-selectivity
and
complete
reaction
pattern
is
not
available.
Here,
we
present
systematic
computational
studies
on
ruthenium-catalyzed
C-H
with
primary,
secondary,
tertiary
alkyl
bromides
aryl
bromides.
The
scission
formation
were
carefully
examined.
Monocyclometalated
ruthenium(II)
complexes
identified
active
species,
which
then
underwent
inner-sphere
single
electron
transfer
(ISET)
activate
organic
results
from
competition
between
close-shell
reductive
elimination
open-shell
radical
coupling.
Based
this
understanding,
multilinear
regression
model
was
built
predict
site-selectivity,
further
validated
by
experiments.
