Angewandte Chemie,
Journal Year:
2020,
Volume and Issue:
132(32), P. 13375 - 13382
Published: April 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.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(22), P. 4835 - 4839
Published: May 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,
Journal Year:
2020,
Volume and Issue:
7(8), P. 1022 - 1060
Published: Jan. 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,
Journal Year:
2024,
Volume and Issue:
14(8), P. 6009 - 6015
Published: April 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,
Journal Year:
2020,
Volume and Issue:
59(32), P. 13273 - 13280
Published: April 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.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(17), P. 6914 - 6918
Published: Aug. 26, 2019
Benzidine
was
found
to
be
a
novel
transient
directing
group
enable
Pd-catalyzed
direct
selenylation
of
inert
C(sp2)–H
bonds
benzaldehydes.
Diverse
diarylselenides
were
readily
constructed
in
high
efficiency
and
satisfactory
yields
with
good
functional
tolerance.
The
practical
usage
the
method
further
demonstrated
by
enlarged
reaction
gram
scale
application
facile
access
two
selenoxanthenes
one
fluorescent
probe.
Organic Letters,
Journal Year:
2018,
Volume and Issue:
20(19), P. 6112 - 6116
Published: Sept. 26, 2018
A
regioselective
rhodium-catalyzed
thiolation
of
N-tosyl
acrylamides
with
readily
available
disulfides
has
been
developed.
Through
N-tosylamide-assisted
activation
the
alkenyl
C(sp2)–H
bond,
a
series
(Z)-alkenyl
sulfides
were
constructed
in
moderate
to
excellent
yields
good
tolerance
functional
groups.
Turnover
numbers
(TONs)
up
7100
obtained
utilizing
0.01
mol
%
RhIII
catalyst.
In
addition,
diphenyl
diselenide
was
also
successfully
applied
this
reaction
for
construction
(Z)-β-alkenyl
selenides
under
identical
conditions.
Dalton Transactions,
Journal Year:
2019,
Volume and Issue:
48(27), P. 9851 - 9905
Published: Jan. 1, 2019
Recent
outstanding
advances
in
the
C–Se
bond
formation
through
transition
metalcatalysed
direct
selanylation,
providing
new
insights
into
their
mechanistic
aspects,
were
provided
this
perspective.
European Journal of Organic Chemistry,
Journal Year:
2018,
Volume and Issue:
2019(1), P. 41 - 45
Published: Oct. 17, 2018
A
convenient
and
effective
protocol
for
the
ruthenium‐catalyzed
C–H
selenylations
of
benzamide
was
achieved
under
mild
reaction
conditions.
The
robust
ruthenium
catalyst
tolerated
a
wide
range
functional
groups
set
stage
preparation
diversely
decorated
benzamides.
amide
directing
group
could
be
transferred
to
carboxylic
acid,
aldehyde
tetrazoles.
Preliminary
mechanistic
study
indicated
base‐assisted
electrophilic‐type
substitution
activation
event.
European Journal of Organic Chemistry,
Journal Year:
2019,
Volume and Issue:
2019(7), P. 1588 - 1593
Published: Jan. 19, 2019
A
novel
palladium(II)/copper(II)‐catalyzed
sulfidation
of
the
C–H
bond
in
electron‐rich
arenes
and
pentafluorobenzene
with
disulfides
was
developed.
This
catalytic
system
can
be
used
to
efficiently
produce
various
types
either
unsymmetrical
aryl
sulfides
or
alkyl
sulfides.
The
present
protocol
could
also
applied
direct
preparation
selenides
via
selenation.
