Photocatalytic Thio/Selenosulfonylation–Bicyclization of Indole-Tethered 1,6-Enynes Leading to Substituted Benzo[c]pyrrolo[1,2,3-lm]carbazoles
Organic Letters,
Год журнала:
2024,
Номер
26(18), С. 3828 - 3833
Опубликована: Апрель 29, 2024
The
photocatalyzed
radical-triggered
thio/selenosulfonylation–bicyclization
of
indole-tethered
1,6-enynes
has
been
established
for
the
first
time,
enabling
synthesis
various
previously
unreported
thio/selenosulfonylated
benzo[c]pyrrolo[1,2,3-lm]carbazoles
with
moderate
to
good
yields
under
mild
conditions.
reaction
pathway
was
proposed,
consisting
energy
transfer,
homolytic
cleavage,
radical
addition,
5-exo-dig,
coupling,
and
a
Mallory
cascade.
This
approach
exhibits
wide
substrate
compatibility
excellent
tolerability
toward
functional
groups
is
characterized
by
its
remarkable
efficiency
in
both
bond
formation
annulation.
Язык: Английский
Photocatalytic Bicyclization of Indole-Tethered 1,6-Enynes for Diastereoselective Synthesis of Pyrrolo[3,2,1-jk]carbazoles
Organic Letters,
Год журнала:
2024,
Номер
26(18), С. 3810 - 3815
Опубликована: Апрель 28, 2024
A
visible-light-driven
photocatalytic
protocol
is
established
for
the
diastereoselective
synthesis
of
pyrrolo[3,2,1-jk]carbazoles
via
a
radical-triggered
multicomponent
bicyclization
reaction
starting
from
readily
available
indole-tethered
1,6-enynes
and
α-benzyl-α-bromomalonates
under
mild
conditions.
This
approach
exhibits
wide
substrate
compatibility
excellent
tolerability
toward
various
functional
groups
boasts
benefit
efficient
ring
formation
chemical
bond
creation.
Язык: Английский
Copper‐catalyzed radical‐induced annulation‐halo(bi)cyanomethylation of indole‐tethered 1,6‐enynes toward pyrrolo[1,2‐a]indoles
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(17), С. 3578 - 3584
Опубликована: Июнь 18, 2024
Abstract
A
copper‐catalyzed
radical‐induced
annulation‐halocyanomethylation
of
indole‐linked
1,6‐enynes
has
been
established
using
haloacetonitrile
as
radical
precursors,
enabling
the
synthesis
21
cyanomethylated
pyrrolo[1,2‐
a
]indoles
with
yields
ranging
from
42%
to
81%
and
Z
/
E
ratio
up
19:1.
Moreover,
by
adjusting
reaction
temperature,
variation
annulation‐bromobicyanomethylation
process
was
achieved,
resulting
in
production
12
bicyanomethylated
]indole
isomers
41–68%.
The
stereoisomeric
mixture
products
could
be
purified
their
pure
configurations
through
recrystallization.
proposed
mechanism
formulated
series
control
experiments.
Язык: Английский
Accessing pyrrolo[1,2-a]indole derivatives via visible-light-induced dearomatizative cyclization of indoles
Chemical Communications,
Год журнала:
2024,
Номер
60(37), С. 4902 - 4905
Опубликована: Янв. 1, 2024
Dearomatizative
cyclization
of
indoles:
a
novel
synthetic
method
for
pyrrolo[1,2-
]indole
derivatives
through
visible-light-induced
cascade
dearomatizative
indoles
with
external
nucleophiles
has
been
developed.
Язык: Английский
Photocatalyzed Annulation‐Biselenylation of Enynone with Diarylselenides toward Biselenium‐Substituted 1‐Indanones under Metal‐ and Photosensitizer‐Free Conditions
Chinese Journal of Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 17, 2025
Comprehensive
Summary
A
practical
photocatalytic
annulation‐biselenylation
strategy
has
been
developed
for
the
efficient
synthesis
of
biselenium‐substituted
1‐indanones
(38
examples
in
total)
with
generally
good
yields
(up
to
95%)
and
excellent
stereoselectivity
(>19
:
1
Z
/
E
ratio)
by
employing
enynones
diaryl
selenides
as
starting
materials
under
photosensitizer‐free
conditions.
The
reaction
mechanism
involves
a
cascade
process
comprising
homolytic
cleavage,
radical
addition,
5‐
exo
‐
dig
cyclization,
capture,
enabling
sequential
formation
multiple
bonds,
such
C(sp
3
)‐Se,
)‐C(sp
2
),
)‐Se
rapidly
construct
molecular
complexity.
Notably,
this
approach
demonstrates
wide
substrate
compatibility
tolerability
towards
various
functional
groups.
It
is
further
characterized
its
remarkable
efficiency
creating
chemical
bonds
achieving
high
atomic
utilization
100%.
Язык: Английский
Reactions of alkynes with C–S bond formation: recent developments
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(32), С. 6443 - 6484
Опубликована: Янв. 1, 2024
Alkynes
are
important
in
organic
synthesis.
This
review
mainly
focuses
on
the
recent
advances
(2013–2023)
alkynes
with
C–S
bond
formation,
based
more
than
30
kinds
of
sulfur
reagents.
Язык: Английский
Assembly of Thiazino[3,4‐a]isoquinoline and Thiazepino[5,4‐a]isoquinoline Frameworks from Isoquinolinium 1,4‐Zwitterionic Thiolates via [5 + 1] and [5 + 2] Cycloaddition Reactions
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 18, 2024
Abstract
Two
cycloaddition
modes
of
isoquinolinium
1,4‐zwitterionic
thiolates
have
been
established.
Upon
choosing
α
‐bromo
ketones
as
the
counterpart,
a
range
isoquinoline‐fused
thiazines
can
be
attained
with
yields
ranging
from
moderate
to
excellent
through
formal
[5+1]
reaction
pathway,
exhibiting
remarkable
substrate
adaptability
and
resilience
diverse
functional
groups.
Additionally,
library
unprecedented
thiazepino[5,4‐
]isoquinolines,
novel
category
seven‐membered
heterocycles,
has
synthesized
via
[5+2]
pathway
utilizing
acetylenedicarboxylate
reactive
component.
Notably,
this
process
stands
out
for
its
exceptional
100
%
atomic
utilization
efficiency.
Язык: Английский
Photo‐catalyzed Stereospecific Synthesis of Trisubstituted Alkenes Incorporating 3,3‐Difluoro‐γ‐Lactams from Morita‐Baylis‐Hillman Acetates and N‐Allylbromodifluoroacetamides
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 1, 2024
Abstract
A
photocatalytic
methodology
has
been
devised
for
the
stereoselective
construction
of
trisubstituted
alkenes
incorporating
3,3‐difluoro‐γ‐lactams
in
17–93%
yields
via
a
radical
cascade
process
utilizing
MBH
acetates
and
N
‐allylbromodifluoroacetamides
as
starting
materials.
The
reaction
mechanism
involves
single‐electron
transfer,
5
‐
exo
trig
cyclization,
addition,
elimination
fashion.
Язык: Английский