Angewandte Chemie,
Год журнала:
2024,
Номер
136(38)
Опубликована: Июнь 21, 2024
Abstract
In
this
study,
we
introduce
a
novel
intramolecular
hydrogen
atom
transfer
(HAT)
reaction
that
efficiently
yields
azetidine,
oxetane,
and
indoline
derivatives
through
mechanism
resembling
the
carbon
analogue
of
Norrish‐Yang
reaction.
This
process
is
facilitated
by
excited
triplet‐state
carbon‐centered
biradicals,
enabling
1,5‐HAT
suppressing
critical
1,4‐biradical
intermediates
from
undergoing
Norrish
Type
II
cleavage
reaction,
pioneering
unprecedented
1,6‐HAT
reactions
initiated
alkenes.
We
demonstrate
synthetic
utility
compatibility
method
across
various
functional
groups,
validated
scope
evaluation,
large‐scale
synthesis,
derivatization.
Our
findings
are
supported
control
experiments,
deuterium
labeling,
kinetic
studies,
cyclic
voltammetry,
Stern–Volmer
density
theory
(DFT)
calculations.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(19), С. 3182 - 3210
Опубликована: Авг. 1, 2023
Abstract
Heterocyclic
scaffolds
are
beneficial
structural
architects
in
a
wide
range
of
pharmaceuticals,
agrochemicals,
biological
and
also
functional
materials.
In
this
regard,
several
investigations
have
been
performed
to
synthesize
them.
Among
these,
visible
light‐induced
difunctionalization
cyclization
strategy
provides
attractive
solutions
by
adopting
greener
routes,
breaking
the
monopoly
conventional
thermal
processes.
A
review
on
these
methodologies
is
desirable
as
unsaturated
aliphatics,
especially
alkenes
one
cheapest
feedstocks
available.
They
offer
diverse
options
modifications
generate
different
products,
including
heterocycles,
which
highly
sought
after
due
their
applications
various
sectors.
To
account
for
advancements
strategy,
we
summarized
light
induced
strategies
that
directly
lead
synthesis
heterocyclic
from
C−C
bonds.
We
categorized
relevant
reaction
schemes
into
four
mechanistically
distinct
sections
namely
(i)
Two
component
oxidative
annulations
(ii)
Radical
mediated
(iii)
Polar
radical
crossover
(iv)
Three
annulations.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(6), С. 1775 - 1781
Опубликована: Янв. 1, 2024
We
have
successfully
demonstrated
an
efficient
and
practical
Pd-catalyzed
reaction
between
aziridine
isocyanide,
leading
to
the
synthesis
of
isoindoline
derivatives
in
moderate
good
yields.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(23), С. 5876 - 5885
Опубликована: Янв. 1, 2023
A
visible-light-mediated
strategy
for
the
efficient
conversion
of
(2-vinylaryl)methanol
derivatives
to
aryl
aldehydes
or
ketones
has
been
developed.
The
plausible
reaction
mechanism
verified
by
a
series
mechanistic
studies.
Organic Letters,
Год журнала:
2024,
Номер
26(21), С. 4548 - 4553
Опубликована: Май 17, 2024
gem-Difluoroalkenes
and
monofluorinated
cycloalkenes
have
emerged
as
basic
structural
units
in
a
variety
of
bioactive
molecules
natural
products.
Thus,
developing
straightforward
efficient
methods
for
synthesizing
fluorinated
alkene
compounds
is
considerable
significance.
Herein,
we
disclose
visible-light-induced
defluorination
2-trifluoromethyl-1-alkene
via
1,5-HAT
process
using
N-alkoxyphtalimides
both
radical
precursor
potential
nucleophile.
The
mild
stepwise
reaction
leads
to
structurally
diverse
gem-difluoroalkenes
cyclooctenes
with
high
efficiency,
respectively.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(38)
Опубликована: Июнь 21, 2024
In
this
study,
we
introduce
a
novel
intramolecular
hydrogen
atom
transfer
(HAT)
reaction
that
efficiently
yields
azetidine,
oxetane,
and
indoline
derivatives
through
mechanism
resembling
the
carbon
analogue
of
Norrish-Yang
reaction.
This
process
is
facilitated
by
excited
triplet-state
carbon-centered
biradicals,
enabling
1,5-HAT
suppressing
critical
1,4-biradical
intermediates
from
undergoing
Norrish
Type
II
cleavage
reaction,
pioneering
unprecedented
1,6-HAT
reactions
initiated
alkenes.
We
demonstrate
synthetic
utility
compatibility
method
across
various
functional
groups,
validated
scope
evaluation,
large-scale
synthesis,
derivatization.
Our
findings
are
supported
control
experiments,
deuterium
labeling,
kinetic
studies,
cyclic
voltammetry,
Stern-Volmer
density
theory
(DFT)
calculations.
Organic Letters,
Год журнала:
2024,
Номер
26(27), С. 5752 - 5757
Опубликована: Июль 1, 2024
A
new
self-cyclopropanation
of
1,3-diphenylpropane-1,3-dione,
leading
to
tetrasubstituted
cyclopropane
containing
three
contiguous
stereogenic
centers
with
high
stereoselectivity,
has
been
achieved
through
violet-light-emitting
diode-irradiated
photocatalysis,
featuring
both
cycloaddition
and
a
distinctive
rearrangement.
Diverging
from
conventional
cyclopropanation
pathways,
this
reaction
yields
unprecedented
rearrangement
cascade
reactions.
Chemical Science,
Год журнала:
2024,
Номер
15(43), С. 17962 - 17970
Опубликована: Янв. 1, 2024
Herein,
we
report
the
first
visible-light-induced
strategy
for
rapid
synthesis
of
densely
functionalized
α-
and
γ-phosphorylated
β-sulfonyl
enamines
in
a
regio-
stereoselective
manner
from
N
-sulfonyl
allenamides
H-phosphine
oxides.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(22), С. 4548 - 4558
Опубликована: Окт. 8, 2024
Abstract
The
synthesis
of
β‐lactam
scaffolds
is
paramount
importance
due
to
their
extensive
applications
in
pharmaceuticals,
particularly
as
antibiotics.
Visible
light
photocatalysis
has
emerged
a
revolutionary
approach
this
domain,
providing
sustainable
and
efficient
pathway
for
construction.
In
review,
we
meticulously
discuss
the
recent
developments
photocatalysed
frameworks.
A
key
focus
Staudinger
reaction,
traditionally
cornerstone
synthesis,
its
adaptation
visible
photocatalysis.
We
explore
mechanistic
intricacies
reaction
under
photochemical
conditions,
along
with
other
pivotal
cyclization
strategies
enabled
by
light.
By
illuminating
novel
photocatalytic
routes
β‐lactams,
review
provides
thorough
understanding
state‐of‐the‐art
techniques
sets
stage
future
innovations
green
these
critical
compounds.
