Chemistry - A European Journal,
Год журнала:
2018,
Номер
25(10), С. 2442 - 2446
Опубликована: Дек. 3, 2018
Abstract
A
metal‐free,
phosphine‐catalyzed
intramolecular
“umpolung
Michael
addition”
on
alkynes
to
form
spiroindol(en)ines
is
reported.
This
nucleophilic
catalysis
enables
the
formation
of
a
wide
scope
five‐
and
six‐membered
in
moderate
excellent
yields
batch
as
well
under
continuous‐flow
conditions.
Triphenylphosphine‐catalyzed
activation
allows
exclusive
exo
‐product
mild
reaction
Chemical Society Reviews,
Год журнала:
2018,
Номер
47(11), С. 3831 - 3848
Опубликована: Янв. 1, 2018
This
tutorial
review
provides
a
good
introduction
to
spirocyclization
reactions
of
indole
derivatives
and
highlights
the
recent
advances
in
construction
spiroindolines
spiroindoles.
Chemistry - A European Journal,
Год журнала:
2018,
Номер
24(28), С. 7228 - 7234
Опубликована: Март 9, 2018
The
ability
of
metal
clusters
involving
elements
from
group
11
(Ag,
Cu,
Au)
to
favorably
interact
with
π
systems
different
size
and
electronic
nature
was
evaluated
at
the
PBE0-D3/def2-TZVPP//PBE0-D3/def2-TZVP
level
theory.
M9
(M=Cu,
Ag,
were
used
as
σ-hole
σ-lump
donors,
benzene,
trifluorobenzene,
hexafluorobenzene
aromatic
rings.
In
addition,
study
expanded
analysis
extended
by
using
naphthalene
anthracene
well
their
corresponding
perfluorinated
derivatives.
Furthermore,
Bader's
theory
Atoms
in
Molecules
natural
bonding
orbital
spin-density
calculations
further
investigate
characterize
regium-π
complexes
described
herein.
Apparently,
bonds
have
not
previously
been
literature
may
be
great
importance
understanding
organocatalytic
processes
substrates
design
new
materials
based
on
this
novel
subclass
bonding.
ACS Catalysis,
Год журнала:
2018,
Номер
9(1), С. 504 - 510
Опубликована: Дек. 4, 2018
A
one-pot
protocol
for
the
dearomatizing
spirocyclization/cross-coupling
of
alkyne-tethered
indoles/pyrroles
is
described.
Mechanistic
studies
support
a
process
by
which
palladium
complexes
generated
in
situ
act
as
both
π-acid
and
cross-coupling
catalysts.
Overall,
this
facilitates
an
efficient
cascade
that
enables
simultaneous
preparation
synthetically
challenging
quaternary
spirocyclic
carbons
tetrasubstituted
alkenes
single
operation.
ACS Catalysis,
Год журнала:
2018,
Номер
8(4), С. 3673 - 3677
Опубликована: Март 19, 2018
The
thorium
methyl
and
hydride
complex
(C5Me5)2ThMe2
[(C5Me5)2Th(H)(μ-H)]2
catalyzed
highly
1,2-regioselective
dearomatization
of
pyridines
via
a
hydroboration
process
is
reported
herein.
Twelve
different
kinds
meta-
para-substituted
are
applicable
to
this
reaction,
giving
the
corresponding
N-boryl-1,2-dihydropyridine
products
in
high
yields.
Other
N-heteroaromatic
compounds,
such
as
benzo-fused
N-heterocycles,
pyrazines,
pyrimidines,
1,3,5-triazine,
benzothiazole,
were
also
found
be
hydroborated
with
chemoselectivity.
Kinetics
including
isotope
effect
studies
revealed
first-order
dependence
on
concentration
catalyst,
pyridine,
pinacolborane,
release
dearomatized
final
product
rate-determining
step.
A
plausible
mechanism
proposed
basis
stoichiometric
reactions
kinetic
studies.
Organic Letters,
Год журнала:
2022,
Номер
24(2), С. 668 - 674
Опубликована: Янв. 5, 2022
Indole-ynones
have
been
established
as
general
substrates
for
radical
dearomatizing
spirocyclization
cascade
reactions.
Five
distinct
and
varied
synthetic
protocols
developed─cyanomethylation,
sulfonylation,
trifluoromethylation,
stannylation
borylation─using
a
variety
of
generation
modes,
ranging
from
photoredox
catalysis
to
traditional
AIBN
methods.
The
simple
easily
prepared
indole-ynones
can
be
used
rapidly
generate
diverse,
densely
functionalized
spirocycles
the
potential
become
routinely
explore
reactivity.
Experimental
computational
investigations
support
proposed
mechanism
suggest
that
other
new
methods
are
now
primed
development.
