Synlett,
Год журнала:
2023,
Номер
35(13), С. 1465 - 1470
Опубликована: Окт. 31, 2023
Abstract
The
development
of
concise
and
efficient
methods
to
construct
bithiophene
derivatives
is
an
appealing
task
in
the
fields
organic
chemistry
functional
materials.
Herein,
we
summarize
our
recent
efforts
towards
catalytic
oxidative
C–H
cyclization
reactions
thiophenol
with
1,3-diynes,
which
provides
a
straightforward
effective
synthetic
approach
both
symmetrical
nonsymmetrical
3,3′-bibenzothiophenes.
This
work
expected
stimulate
application
annulation
aromatics
1,3-diynes
for
exploitation
Organic Letters,
Год журнала:
2023,
Номер
25(12), С. 2063 - 2067
Опубликована: Март 20, 2023
A
novel
copper-catalyzed
tandem
cyclization/direct
C(sp2)–H
annulation
of
phenyl
azide–ynamides
via
α-imino
copper
carbenes
has
been
developed,
which
provides
a
concise
and
flexible
approach
for
the
construction
range
valuable
azepino[2,3-b:4,5-b′]diindoles
in
mostly
good
to
excellent
yields
with
high
chemoselectivities.
This
reaction
also
exhibits
broad
substrate
scope,
functional
group
tolerance,
simple
operation,
mild
conditions.
A
novel
tandem
reaction
involving
amino-substituted
ynones
and
cyclic
carbonyls
has
been
developed,
efficiently
synthesizing
3,4-fused
pyrroles
with
seven-membered
carbocycles
by
a
one-pot
method.
This
proceeds
through
cascade
ring-expansion
of
carbonyls,
followed
intramolecular
cyclization
reactions.
metal-free
strategy
enables
the
concurrent
construction
medium-sized
ring
pyrrole
ring,
exhibiting
high
step
economy.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(16), С. 11377 - 11391
Опубликована: Авг. 4, 2023
Over
the
past
two
decades,
synthetic
strategies
for
synthesizing
skeletons
of
various
indole
alkaloids
based
on
tryptamine-ynamide
have
been
continuously
developed
and
applied
to
total
syntheses
or
formal
related
molecules.
In
this
synopsis,
we
summarized
cyclization
pathways
under
different
catalytic
conditions,
emphasizing
reaction
mechanism
applications
in
alkaloids.
Here,
an
Ir/Zn-cocatalyzed
atroposelective
[2+2+2]
cycloaddition
of
1,6-diynes
and
ynamines
was
developed,
forging
various
functionalized
C─N
axially
chiral
indoles
pyrroles
in
generally
good
to
excellent
yields
(up
99%),
chemoselectivities,
high
enantioselectivities
98%
enantiomeric
excess)
with
wide
substrate
scope.
This
cocatalyzed
strategy
not
only
provided
alternative
promising
reliable
way
for
asymmetric
alkyne
cyclotrimerization
easy
handle
but
also
settled
the
issues
previous
[Rh(COD)2]BF4-catalyzed
system
on
construction
axial
chirality
such
as
complex
operations,
limited
scope,
low
efficiency.
In
addition,
control
experiments
theoretical
calculations
disclosed
that
Zn(OTf)2
markedly
reduced
barrier
migration
insertion
significantly
increase
reaction
efficiency,
which
distinctly
different
from
work
Lewis
acid
improving
yield
through
accelerating
oxidative
addition
reductive
elimination.
Organic Letters,
Год журнала:
2023,
Номер
25(17), С. 3034 - 3039
Опубликована: Апрель 24, 2023
A
catalyst-controlled
divergent
synthesis
of
bridged
[3.3.1]
bis(indolyl)-oxanes
and
cis-[6.7]
fused
bis(indolyl)
oxepanes
via
diastereoselective
desymmetrization
bis(indolyl)-cyclohexadienones
is
presented
for
the
first
time.
The
reaction
highly
atom-
step-economic,
furnishing
sp3-rich
functionalized
derivatives
in
good
to
excellent
yields
with
wide
substrate
scope.
proceeds
through
Friedel-Crafts
alkylation
followed
by
selective
C-C
bond
formation/rearrangement.
Gram
scale
synthetic
utility
generate
alkaloid-like
molecular
diversity
were
also
illustrated.
Green Chemistry,
Год журнала:
2023,
Номер
25(20), С. 8124 - 8133
Опубликована: Янв. 1, 2023
Environmentally
friendly
acid-catalyzed
2-alkynyl-ynamides
(N–Csp)
bond
cleavage,
alkyne
migration
and
stereospecific
functionalization
with
anisole
derivatives
for
the
synthesis
of
challenging
indole
scaffolds
in
5–10
minutes.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 30, 2024
Due
to
the
inherent
challenges
posed
by
linear
coordination
of
gold(I)
complexes,
asymmetric
gold-catalyzed
processes
remain
challenging,
particularly
in
atroposelective
synthesis
axially
chiral
skeletons.
Except
for
extremely
few
examples
intramolecular
annulations,
construction
axial
chirality
via
intermolecular
alkyne
transformation
is
still
undeveloped.
Herein,
a
gold/HNTf
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(28), С. 5737 - 5741
Опубликована: Янв. 1, 2023
A
Pd(
ii
)
catalyzed
syn
-symmetrical
diarylation
of
ynamides
has
been
showcased
utilizing
readily
available
arylboronic
acids
as
nucleophilic
arylating
agents.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(7), С. 1615 - 1626
Опубликована: Фев. 7, 2024
Abstract
Herein,
we
describe
a
base‐promoted
regioselective
and
chemoselective
cascade
cyclization,
ynamide
N−C
sp
bond
cleavage,
selective
intramolecular
1,3‐migration,
simultaneous
N
‐desulfonylation
strategy
for
the
synthesis
of
2‐phenyl‐3‐(phenylethynyl)‐1H‐indole
derivatives.
We
observed
multiple
breaking
(−N−Ts,
C
2
−Ts,
−I/C
−SePh)
from
(
E
)‐3‐(1‐iodo‐2‐phenyl‐2‐tosylvinyl)‐2‐phenyl‐1‐tosyl‐indole/(
)‐2‐phenyl‐3‐(2‐phenyl‐1‐(phenylselanyl)‐2‐tosylvinyl)‐1‐tosyl‐indole
derivatives
to
prepare
in
15–60
min
using
our
standard
reaction
conditions.
A
gram‐scale
experiment
as
well
postsynthetic
transformations
synthesized
were
performed
exhibit
advantages
this
synthetic
methodology.
Organic Letters,
Год журнала:
2024,
Номер
26(31), С. 6586 - 6590
Опубликована: Июль 30, 2024
A
rhodium-catalyzed
[4
+
2]
cycloaddition
of
ynamines
and
2-(cyanomethyl)phenylboronates
has
been
developed,
leading
to
efficient
excellent
regioselective
synthesis
valuable
indole-linked
aromatic
compounds
in
a
concise
flexible
approach.
Interestingly,
this
strategy
was
successful
the
construction
C···N
axially
chiral
indoles
with
high
enantiocontrol
by
introduction
new
phosphoramidite
ligand
(Xie-Phos).
