Handbook of CH‐Functionalization,
Год журнала:
2022,
Номер
unknown, С. 1 - 24
Опубликована: Окт. 1, 2022
Abstract
This
article
describes
recent
advances
in
C–heteroatom
bond
formation
via
ruthenium‐catalyzed
proximal
or
remote
C(sp
2
)H
functionalization.
ruthenium
catalysis
is
particularly
fascinating
not
only
because
of
the
low
cost
metal,
but
also
it
allows
for
a
wide
range
transformations.
The
excellent
reactivity
catalysts
attributed
to
highly
active
CH
ruthenated
intermediate,
which
can
perform
oxidative
addition
electrophilic
substitution
at
ortho
position
as
well
radical
distal
meta
para
positions.
Diverse
strongly
weakly
coordinating
directing
groups,
such
N
‐containing
heterocycles,
aldehydes,
ketones,
carboxylic
acids,
amides,
sulfamides,
carbamates,
and
phosphines,
assist
functionalization
ortho,
meta,
even,
positions
CN,
CO,
C–halogen,
CSi,
CS/Se,
CB
bond‐forming
reactions.
Typically,
[RuCl
(
p
‐cymene)]
used
construction,
octahedral
Ru
RuHCl(CO)(PPh
3
)
(CO)
12
have
been
CSi
CN
formation,
respectively.
In
addition,
this
details
representative
applications
Ru‐catalyzed
preparation
late‐stage
modification
important
synthetic
building
blocks
pharmaceuticals.
Chemical Reviews,
Год журнала:
2022,
Номер
122(21), С. 16110 - 16293
Опубликована: Сен. 16, 2022
In
the
present
review,
we
discuss
recent
progress
in
field
of
C–Z
bond
formation
reactions
(Z
=
S,
Se,
Te)
catalyzed
by
transition
metals.
Two
complementary
methodologies
are
considered─catalytic
cross-coupling
and
catalytic
addition
reactions.
The
development
advanced
systems
is
aimed
at
improved
catalyst
efficiency,
reduced
loading,
better
cost
environmental
concerns,
higher
selectivity
yields.
important
rise
research
efforts
sustainability
green
chemistry
areas
critically
assessed.
paramount
role
mechanistic
studies
a
new
generation
addressed,
key
achievements,
problems,
challenges
summarized
for
this
field.
Organic Letters,
Год журнала:
2024,
Номер
26(22), С. 4835 - 4839
Опубликована: Май 29, 2024
A
three-component
cascade
reaction
involving
cyclohexanones,
anilines,
and
diaryl
diselenides
under
metal-free
conditions
is
reported.
The
ortho-selenation
of
cyclohexanones
with
diselenides,
followed
by
sequential
dehydroaromatization
enables
the
preparation
a
variety
o-selanyl
anilines
in
moderate
to
excellent
yields.
This
innovative
transformation
notable
for
its
tolerance
functional
groups
suitable
late-stage
modification
complex
pharmaceuticals.
Organic Chemistry Frontiers,
Год журнала:
2020,
Номер
7(8), С. 1022 - 1060
Опубликована: Янв. 1, 2020
This
review
summarizes
recent
advances
in
C–S
and
C–Se
formationsviatransition
metal-catalyzed
C–H
functionalization
utilizing
directing
groups
to
control
the
site-selectivity.
ACS Catalysis,
Год журнала:
2024,
Номер
14(8), С. 6009 - 6015
Опубликована: Апрель 5, 2024
Rhodium(III)-catalyzed
atroposelective
C–H
selenylation
of
1-aryl
isoquinolines
has
been
achieved.
The
direct
reaction
between
and
2-(phenylselanyl)isoindoline-1,3-dione
in
the
presence
chiral
SCpRh(III)
complex
afforded
a
series
axially
isoquinoline
selenides
up
to
95%
yield
96%
ee.
features
mild
conditions
broad
substrate
scope.
DFT
calculations
revealed
that
C–Se
bond
formation
step
proceeds
through
formal
SN2
pathway.
Angewandte Chemie International Edition,
Год журнала:
2020,
Номер
59(32), С. 13273 - 13280
Опубликована: Апрель 13, 2020
Abstract
Conventional
direct
C−H
selenylation
suffers
from
simple
selenation
with
limited
atom
economy
and
complicated
reaction
system.
In
this
work,
we
designed
benzoselenazolone
as
a
novel
bifunctional
selenide
reagent
for
both
off‐
on‐DNA
under
rhodium(III)
catalysis.
We
show
that
using
allowed
production
of
series
products
containing
an
adjacent
aminoacyl
group
in
fast
efficient
way,
high
economy.
The
synthetic
application
method
was
demonstrated
by
taking
advantage
the
amide
functionality
nucleophile,
directing
group,
coupling
partner.
This
work
shows
great
potential
facilitating
rapid
construction
selenium‐containing
DNA‐encoded
chemical
libraries
(SeDELs),
lays
foundation
development
drugs.
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
364(4), С. 838 - 844
Опубликована: Дек. 17, 2021
Abstract
A
convenient
and
effective
method
of
ruthenium‐catalyzed
C−H/N−H
annulations
using
vinylene
carbonate
as
oxidizing
acetylene
surrogate
has
been
disclosed.
This
is
scalable
compatible
with
a
wide
range
functional
groups,
providing
step‐economical
access
to
indole
synthesis
Preliminary
mechanistic
studies
provided
support
for
reversible,
acetate‐assisted
C−H
ruthenation,
along
subsequent
olefin
insertion.
magnified
image
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(10), С. 2075 - 2080
Опубликована: Янв. 1, 2024
Direct
C(sp
3
)-H
selenation,
which
is
most
atom
economical,
remains
a
formidable
challenge,
and
only
few
examples
have
been
reported
to
date.
In
this
article,
we
introduce
the
transition
metal-free
selenation
with
β-ketosulfones
diselenides
as
material
source.
Advanced Synthesis & Catalysis,
Год журнала:
2020,
Номер
362(24), С. 5708 - 5715
Опубликована: Окт. 27, 2020
Abstract
A
convenient
and
effective
method
of
palladium‐catalyzed
C−H
selenylation
the
2‐aryl
acetamides
assisted
with
removable
8‐aminoquinoline
readily
available
diselenides
selenyl
chlorides
has
been
developed.
This
reaction
is
scalable
tolerates
a
wide
range
functional
groups,
providing
straightforward
way
preparing
unsymmetrical
diaryl
selenides
dibenzoselene‐pinone.
Preliminary
mechanistic
studies
indicated
that
single‐electron
transfer
type
mechanism
facile
metalation
are
operative.
magnified
image
Chemistry - A European Journal,
Год журнала:
2020,
Номер
26(69), С. 16450 - 16454
Опубликована: Июнь 29, 2020
Abstract
C−H
hydroxylation
of
aryl
acetamides
and
alkyl
phenylacetyl
esters
was
accomplished
via
challenging
distal
weak
O‐
coordination
by
versatile
ruthenium(II/IV)
catalysis.
The
ruthenium(II)‐catalyzed
oxygenation
proceeded
through
activation,
oxidation
reductive
elimination,
thus
providing
step‐economical
access
to
valuable
phenols.
p
‐cymene‐ruthenium(II/IV)
manifold
established
detailed
experimental
DFT‐computational
studies.
