ACS Catalysis,
Год журнала:
2021,
Номер
11(18), С. 11579 - 11587
Опубликована: Сен. 3, 2021
Unique
reactivity
of
diphenylacetylene
has
been
uncovered
through
weak
chelation-assisted
cobalt-catalyzed
regioselective
C(4)–H
activation
3-pivolyl
indole.
α-Hydroxy
ketone
and
α,β-unsaturated
derivatives
have
synthesized
in
good
yields
from
indole
alkynes.
Notably,
the
C(4)–H-functionalized
product
was
obtained
with
high
stereo-
regioselectivity
simply
by
changing
coupling
partner
symmetrical
alkynes
to
unsymmetrical
aromatic-aliphatic
Most
importantly,
trifluoroethanol
acts
as
a
sole
source
water
for
this
conversion.
Quantitative
detection
bis(2,2,2-trifluoroethyl)
ether
dry
19F
NMR
LCMS
studies
indirectly
confirms
situ
formation
water.
A
six-membered
cobaltacycle
intermediate
detected
HRMS,
also,
further
confirmed
quantum
mechanical
calculations,
which
accounts
highly
functionalization.
Chemical Reviews,
Год журнала:
2022,
Номер
122(15), С. 12544 - 12747
Опубликована: Июль 17, 2022
1,1,1,3,3,3-Hexafluoroisopropanol
(HFIP)
is
a
polar,
strongly
hydrogen
bond-donating
solvent
that
has
found
numerous
uses
in
organic
synthesis
due
to
its
ability
stabilize
ionic
species,
transfer
protons,
and
engage
range
of
other
intermolecular
interactions.
The
use
this
exponentially
increased
the
past
decade
become
choice
some
areas,
such
as
C–H
functionalization
chemistry.
In
review,
following
brief
history
HFIP
an
overview
physical
properties,
literature
examples
reactions
using
or
additive
are
presented,
emphasizing
effect
each
reaction.
Organic & Biomolecular Chemistry,
Год журнала:
2020,
Номер
18(43), С. 8793 - 8809
Опубликована: Янв. 1, 2020
Sulfur
ylides
first
disclosed
in
1930
started
to
gain
more
attention
the
1960s,
thanks
mainly
studies
by
Corey
and
Chaykovsky
on
their
use
for
preparation
of
strained
rings.
More
recently,
chemistry
these
compounds
has
experienced
important
growth,
part
due
similarity
reactivities
with
diazo
compounds.
This
short
review
provides
an
overview
great
assortment
reactions
sulfoxonium
ylides,
outlining
a
comparison
between
congeners:
sulfonium
Insertion
reactions,
cyclisation
ring-opening
are
highlighted,
giving
particular
catalytic
asymmetric
methodologies.
Chemical Science,
Год журнала:
2021,
Номер
13(5), С. 1192 - 1209
Опубликована: Дек. 8, 2021
Sulfoxonium
ylides
are
important
surrogates
for
diazo
compounds,
and
their
use
in
industry
as
safer
alternatives
has
been
evaluated
during
recent
years.
Beyond
the
known
classical
transformations,
these
have
also
used
a
surprising
plethora
of
novel
intrinsic
chemical
reactions,
especially
Bench
stability
handling
an
advantage
this
class
organosulfur
molecules.
Despite
this,
efficient
asymmetric
specifically
catalytic
enantioselective
versions,
only
recently
reported,
there
specific
reasons
this.
This
perspective
article
covers
topic
from
first
studies
up
to
latest
advances,
giving
personal
perspectives
showing
main
challenges
area
coming
Journal of the American Chemical Society,
Год журнала:
2021,
Номер
143(37), С. 14962 - 14968
Опубликована: Сен. 8, 2021
A
NiH-catalyzed
thioether-directed
cyclometalation
strategy
is
developed
to
enable
remote
methylene
C–H
bond
amidation
of
unactivated
alkenes.
Due
the
preference
for
five-membered
nickelacycle
formation,
chain-walking
isomerization
initiated
by
NiH
insertion
an
alkene
can
be
terminated
at
γ-methylene
site
from
moiety.
By
employing
2,9-dibutyl-1,10-phenanthroline
(L4)
as
ligand
and
dioxazolones
reagent,
occurs
γ-C(sp3)–H
bonds
afford
amide
products
in
up
90%
yield
(>40
examples)
with
remarkable
regioselectivity
(up
24:1
rr).
New Journal of Chemistry,
Год журнала:
2021,
Номер
45(31), С. 13692 - 13746
Опубликована: Янв. 1, 2021
This
review
summarises
a
wide
range
of
transformations
on
the
indole
skeleton,
including
arylation,
alkenylation,
alkynylation,
acylation,
nitration,
borylation,
and
amidation,
using
transition-metal
catalyzed
C–H
functionalization
as
key
step.
Chemistry - An Asian Journal,
Год журнала:
2021,
Номер
16(5), С. 443 - 459
Опубликована: Янв. 15, 2021
Metal
carbenes
play
a
pivotal
role
in
transition-metal-catalyzed
synthetic
transfer
reactions.
The
metal
carbene
is
generated
either
from
diazo
compound
through
facile
extrusion
of
N2
with
catalyst
or
situ
other
sources
like
triazoles,
pyriodotriazoles,
sulfoxonium
ylides
and
iodonium-ylide.
On
the
hand,
Co(III),
Rh(III)
&
Ir(III)-catalyzed
C-H
functionalizations
have
been
well
established
as
key
step
to
enable
construction
various
transformations.
Interestingly,
recent
years,
merging
these
two
concepts
activation
migratory
insertion
gained
much
attention,
particular
group
9
metal-catalyzed
arene
precursors
via
insertion.
In
this
review,
we
summarize
advances
direct
alkylation/alkenylation/arylation
also
discuss
intermediates
within
catalytic
cycles.
Asian Journal of Organic Chemistry,
Год журнала:
2022,
Номер
11(4)
Опубликована: Март 23, 2022
Abstract
In
recent
years,
the
transition‐metal‐catalyzed
functionalization
reactions
of
sulfoxonium
ylides
have
been
explored
extensively
because
their
usefulness
as
carbene‐transfer
agents,
since
they
can
produce
metal
carbenes
through
catalysis.
Moreover,
are
safer
and
advantages
simple
handling
good
stability
over
other
counterparts
like
diazo‐compounds.
This
review
article
attempts
to
highlight
advances
in
metal‐catalyzed
C−H
ylides.
Organic Letters,
Год журнала:
2024,
Номер
26(1), С. 62 - 67
Опубликована: Янв. 3, 2024
We
have
found
a
chameleonic
reactivity
of
imidoyl
sulfoxonium
ylides.
On
the
one
hand,
ylides
react
with
electron-deficient
reagents,
such
as
alkynyl
esters,
to
lead
formation
1,2-dihydro-pyridines.
The
methyl
group
attached
sulfur
atom
acts
methylene
donor.
other
pyridinium
1,4-zwitterionic
thiolates,
which
leads
functionalized
pyrroles.
Both
transformations
feature
mild
reaction
conditions
and
good
functional
tolerance.
Chemistry - An Asian Journal,
Год журнала:
2020,
Номер
15(24), С. 4184 - 4198
Опубликована: Ноя. 9, 2020
Selective
editing
of
the
benzenoid
C-H
bonds
(C4-C7)
in
indoles/indolines
has
received
great
interest
because
functionalized
are
featured
many
marketed
drugs
and
natural
products.
Transition-metal-catalyzed
directed
functionalization
thus
been
developed
to
manipulate
core
through
C-C
C-heteroatom
bond
formation.
This
review
covers
recent
advances
selective
forming
reactions,
alkylation,
alkenylation
alkynylation,
over
ring
using
metal
catalysis.
