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
Construction of C–S and C–Se Bonds via Photocatalytic Aromatization-Driven Deconstructive Diversification of Spiro-Dihydroquinazolinones Derived from Unstrained Ketones
Tao Wang,
Jin‐Long Dai,
Yifeng Jiang
и другие.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 13, 2025
A
novel
and
robust
deconstructive
functionalization
reaction
of
spiro-dihydroquinazolinones
with
sulfenylating
reagents
in
the
presence
base
has
been
realized
under
visible
light
irradiation.
This
enabled
direct
ring-opening
unstrained
cyclic
ring
systems,
producing
skeletally
diverse
functionalized
quinazolinones
moderate
to
good
yields.
range
variety
including
diaryl
disulfide,
thiosulfonate,
dithiosulfonate
1-[(trifluoromethyl)thio]-2,5-pyrrolidinedione
were
compatible
for
this
transformation.
In
addition,
diselenide
selenosulfonate
could
also
couple
form
C-Se
Bonds.
Mechanistic
studies
revealed
that
proceeds
via
a
radical-radical
coupling
pathway.
Язык: Английский
Assembly of Functionalized gem-Difluoroalkenes via Photocatalytic Defluorocyanoalkylation and Defluoroacylation of α-CF3 Styrenes with Oxime Esters
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
We
report
an
efficient
photocatalytic
protocol
for
the
defluorocyanoalkylation
and
defluoroacylation
of
α-trifluoromethyl
styrenes
by
utilizing
oxime
esters
as
radical
donors,
allowing
preparation
diverse
Язык: Английский
Visible Light-Promoted and Catalyst-Controlled α-Aminoalkylation and α-Diaminoalkylation of Morita-Baylis–Hillman Acetates with N-Methyl Arylamines: Divergent Synthesis of N-Containing Alkyl Acrylates and γ,γ-Diaminobutyl Esters
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 2, 2024
Visible
light-promoted
α-aminoalkyl
radical-triggered
α-aminoalkylation
and
α-diaminoalkylation
of
Morita-Baylis–Hillman
acetates
with
N-methyl
arylamines
to
synthesize
N-containing
alkyl
acrylates
γ,γ-diaminobutyl
esters
was
reported.
Photoinduced
is
carried
out
Na2-eosin
Y
as
an
organophotocatalyst
at
room
temperature
under
metal-
oxidant-free
conditions.
In
particular,
the
performed
via
radical
addition/elimination
followed
by
a
catalyst-controlled
selective
addition
strategy
in
one
step
[Ir(dtbbpy)(bpy)2)]PF6/KF
catalytic
system.
The
reaction
highly
atom-
step-economic,
high
selectivity,
furnishing
butyl
moderate
good
yields
wide
substrate
scope.
Язык: Английский
Photoredox-Catalyzed Alkynylation of C(sp3)-H Bonds Adjacent to a Nitrogen Atom of Tertiary Amines with Alkynyl Bromides
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(21), С. 15901 - 15913
Опубликована: Окт. 12, 2024
A
novel
and
robust
alkynylation
of
C(sp3)–H
bonds
adjacent
to
a
nitrogen
atom
tertiary
amines
with
alkynyl
bromides
as
radical
alkynylating
reagents
has
been
realized
under
visible-light
irradiation.
range
variety
including
N-arylamines
N-alkylamine
have
coupled
both
aromatic
aliphatic
furnish
51
examples
propargylamines
in
moderate
excellent
yields
(31–80%
yields).
The
possible
mechanism
was
addition–elimination
process
based
on
preliminary
mechanistic
studies.
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