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.
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.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(10)
Опубликована: Янв. 9, 2024
Abstract
We
present
the
first
example
of
electrocatalytic
three‐component
annulation–iodosulfonylation
indole‐tethered
1,6‐enynes
with
arylsulfonyl
hydrazides
and
KI
for
accessing
various
iodosulfonated
pyrrolo[1,2‐
a
]indoles
in
moderate
to
excellent
yields
high
stereospecificity.
This
electrosynthesis
opens
new
avenues
construction
skeleton
good
functional
group
compatibility
under
environmentally
benign
condition.
Based
on
control
experiments
cyclic
voltammetry
data,
we
suggested
plausible
reaction
mechanism
which
included
anodic
oxidation,
homolysis
iodide,
radical
addition,
5
‐
exo
dig
cyclization,
coupling
or
nucleophilic
attack
iodide
ions
cascade.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(12), С. 1399 - 1406
Опубликована: Фев. 29, 2024
Comprehensive
Summary
A
general
and
convenient
photoredox‐catalyzed
acylation
alkylcyanation
of
MBH
acetates
has
been
established,
enabling
the
assembly
C(sp
2
)–C(sp
3
)
bond
by
a
nitrogen‐centered
radical
strategy
for
synthesis
trisubstituted
alkenes
in
moderate
to
excellent
chemical
yields
(48
examples
total).
The
reaction
with
acyl
(indanone)
oxime
esters
afforded
containing
1,4‐dicarbonyl
groups.
Interestingly,
use
Eosin
Y
as
photocatalyst
catalytic
system
resulted
formation
distal
cyano
group‐anchored
via
deconstructive
functionalization
cycloketone
esters.
Notably,
these
resulting
compounds
could
be
applied
late‐stage
transformations,
providing
important
methods
dihydropyridazin‐3(2
H
)‐one.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(7), С. 4877 - 4887
Опубликована: Март 8, 2024
General
and
convenient
visible-light-promoted
alkylsulfonylation
cyanoalkylsulfonylation
of
MBH
adducts
have
been
developed
through
the
multicomponent
insertion
sulfur
dioxide,
enabling
assembly
two
C–S
bonds
to
generate
structurally
diverse
allylic
alkylsulfones
(43
examples
in
total).
The
reaction
with
potassium
alkyltrifluoroborates
1,4-diazabicyclo[2.2.2]octane
bis(sulfur
dioxide)
adduct
afforded
sulfones
generally
good
yields.
Notably,
addition
N,N,N′,N′-tetramethylethylenediamine
as
a
base
into
photocatalytic
system
led
yielding
an
alkyl
sulfonyl
unit
cyano
group-anchored
trisubstituted
alkenes
by
utilizing
cycloketone
oxime
esters
C-radical
precursors.
Both
these
reactions
constructed
bonds,
all
desired
products
were
obtained
moderate
excellent
yields
complete
stereospecificity.
Molecules,
Год журнала:
2024,
Номер
29(4), С. 782 - 782
Опубликована: Фев. 8, 2024
We
present
the
first
example
of
visible-light-mediated
multicomponent
annulation
1,7-diynes
by
taking
advantage
quadruple
cleavage
olf
carbon-halogen
bonds
BrCCl3
to
generate
a
C1
synthon,
which
was
adeptly
applied
preparation
skeletally
diverse
3-benzoyl-quinolin-2(1H)-one
acetates
in
moderate
good
yields.
Controlled
experiments
demonstrated
that
H2O
acted
as
both
oxygen
and
hydrogen
sources,
gem-dichlorovinyl
carbonyl
compound
exhibited
critical
intermediate
this
process.
The
mechanistic
pathway
involves
Kharasch-type
addition/6-exo-dig
cyclization/1,5-(SN”)-substitution/elimination/binucleophilic
1,6-addition/proton
transfer/tautomerization
sequence.
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%.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(5), С. 3525 - 3537
Опубликована: Фев. 16, 2024
A
photochemical
approach
toward
RCOCF2-substituted
pyrrolo[1,2-a]indolediones
was
developed
by
the
radical
cascade
difluoroalkylation/cyclization
reaction
of
unactivated
1-acryloyl-2-cyanoindoles
with
ethyl
iododifluoroacetate
or
iododifluoramides
under
visible-light
irradiation.
This
transition-metal-
and
photosensitizer-free
protocol
afforded
diverse
difluoroalkylated
in
moderate
to
good
yields
mild
conditions.
Most
appealingly,
can
proceed
smoothly
sunlight
irradiation,
which
opens
a
new
avenue
pyrrolo[1,2-a]indolediones.
Frontiers in Chemistry,
Год журнала:
2024,
Номер
12
Опубликована: Март 26, 2024
The
first
photocatalytic
trichloromethyl
radical-triggered
annulative
reactions
of
amide-linked
1,7-diynes
with
polyhalomethanes
were
established
for
the
flexible
assembly
functionalized
quinolin-2(1H)-ones
generally
acceptable
yields.
With
installation
aryl
group
(R
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
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.
