Photo-Thiocyanoamination of π- and σ-Bonds: Reagent Development and Synthetic Applications
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 29, 2025
1,2-Thiocyanoamines
make
up
a
class
of
important
structural
motifs
that
are
found
in
number
bioactive
molecules
and
precursors
to
many
more.
Despite
their
synthetic
significance,
expedient
access
this
difunctionalization
is
rare.
Herein,
the
development
thiocyanoimination
reagent
disclosed,
taking
advantage
photomediated
energy
transfer
phenomena
for
facile
alkenes.
The
strategy
was
be
viable
σ-bonds
as
well,
providing
generalized
accessing
small
infused
with
amine
-SCN.
Язык: Английский
Photo-Induced Difluoromethylation-Cyclization and Domino Amination-Defluorination to 4-(Aminomethyl)-3-fluoro-quinolinones
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 30, 2024
Herein,
we
report
a
visible
light-induced
difluoromethylation
cyclization
and
subsequent
amination-defluorination
reaction.
This
protocol
allows
efficient
to
valuable
3-fluoro-quinolinones
in
moderate
excellent
yields.
A
sequential
difluoromethylation-cyclization-amination-defluorination
mechanism
was
proposed
based
on
study.
Further
density
functional
theory
(DFT)
calculations
revealed
that
the
base
K
Язык: Английский
A Chromatographic Relay Conjugated Photoredox Strategy: S, Se- Pharmacophore from Alkenes via Formal [2+2+1] Heteroannulation
Chemical Communications,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
A
strategy
involving
alumina
chromatography
coupled
with
photoredox
to
produce
2-amino-dihydrothiophenes
and
their
selenium
analogues
via
a
formal
[2+2+1]
heteroannulation
between
alkenes,
thio(seleno)cyanate,
bromomalonates
is
reported.
Язык: Английский
Visible Light-Induced Copper-Catalyzed Regio- and Stereoselective Difluoroalkylthiocyanation of Alkynes
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 9118 - 9124
Опубликована: Июнь 6, 2024
The
first
regio-
and
stereoselective
difluoroalkylthiocyanation
of
alkynes
with
BrCF
Язык: Английский
Three-Component Photochemical Cyclization/Dithiocarbamate Formation of gem-Difluoro Quinolin-2(1H)-ones
Organic Letters,
Год журнала:
2024,
Номер
26(44), С. 9604 - 9609
Опубликована: Окт. 29, 2024
Herein,
a
novel
visible-light-induced
6-
Язык: Английский
Recent Advances in the Synthesis of Organic Thiocyano (SCN) and Selenocyano (SeCN) Compounds, Their Chemical Transformations and Bioactivity
Molecules,
Год журнала:
2024,
Номер
29(22), С. 5365 - 5365
Опубликована: Ноя. 14, 2024
New
approaches
for
the
synthesis
of
organic
thio-
and
selenocyanates,
methods
to
incorporate
them
into
more
complex
structures,
including
a
wide
variety
heterocyclic
polycylic
derivatives,
are
reviewed.
Protocols
that
convert
SCN
SeCN
moieties
thio
seleno
derivatives
by
transforming
cyano
group
also
examined.
In
representative
cases,
bioactivity
data
these
classes
compounds
Язык: Английский
Visible-light-induced three component difluoromethylation cyclization carbo-thioesterification to CF2-Containing γ-Lactams
Molecular Catalysis,
Год журнала:
2024,
Номер
570, С. 114685 - 114685
Опубликована: Ноя. 21, 2024
Язык: Английский
Synthesis of Alkyl Sulfones via a Photocatalytic Multicomponent Reaction of Aryldiazo Tetrafluoroborate Salts, Styrene Derivatives, and Sodium Metabisulfite
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 25, 2024
Practical
visible-light-induced
synthesis
of
alkyl
sulfones
has
been
achieved
via
a
multicomponent
reaction
aryldiazo
tetrafluoroborate
salts,
styrene
derivatives,
thiophenol
and
sodium
metabisulfite
in
the
presence
rhodamine
B.
Язык: Английский
Visible-light-induced photocatalytic four-component fluoroalkylation–dithiocarbamylation via difunctionalization of styrenes
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(42), С. 8437 - 8452
Опубликована: Янв. 1, 2024
Herein
we
demonstrate
that
a
visible-light-induced
photocatalytic
four-component
fluoroalkylation-dithiocarbamylation
is
unified
method
for
the
fluoroalkylation
of
diverse
activated
fluoroalkyl
halides,
including
monofluoroalkyl
bromides,
difluoroalkyl
trifluoromethyl
iodide,
and
perfluoroalkyl
iodides.
The
synthetic
value
this
has
been
demonstrated
by
transformations
various
substrates
containing
drug/natural
product
skeletons,
gram
scale
reactions,
further
derivatizations
fluorodithiocarbamate
products.
This
work
features
an
atom
economical
protocol
simple
to
operate,
does
not
require
any
additives
or
strong
bases,
can
be
carried
out
under
mild
conditions.
Язык: Английский