Harnessing (Phenylsulfonyl)difluoromethyl Sulfonium Salt: A Radical Approach to Photoredox-Catalyzed Functionalization of Unsaturated Compounds with the PhSO2CF2 Group
JACS Au,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 22, 2025
Язык: Английский
Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis
Peng Wu,
Gabriel Goujon,
Shulei Pan
и другие.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(51)
Опубликована: Сен. 5, 2024
Benzo[1,3,2]dithiazole-1,1,3-trioxides
are
bench-stable
and
easy-to-use
reagents.
In
photoredox
catalysis,
they
generate
methyl
perdeuteromethyl
radicals
which
can
add
to
a
variety
of
radical
acceptors,
including
olefins,
acrylamides,
quinoxalinones,
isocyanides,
enol
silanes,
N-Ts
acrylamide.
As
byproduct,
salt
is
formed
be
regenerated
the
original
methylating
agent.
Flow
chemistry
provides
an
option
for
reaction
scale-up
further
underscoring
synthetic
usefulness
these
methylation
Mechanistic
investigations
suggest
single-electron
transfer
(SET)
pathway
induced
by
catalysis.
Язык: Английский
Photocatalyzed Imino-Difluoromethylation of Alkenes with Bifunctional Oxime Esters
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(18), С. 13585 - 13594
Опубликована: Сен. 11, 2024
Herein,
we
report
a
simple
and
versatile
difluoromethylene-imide
reaction
in
which
series
of
olefins
can
undergo
difluoromethylenimine
under
photocatalytic
conditions
through
an
energy
transfer
(EnT)
process.
The
has
mild
wide
range
applicability.
We
successfully
synthesized
27
molecules
containing
difluoromethylene
units,
featuring
easily
accessible
starting
materials
operational
simplicity.
Язык: Английский
Recent Advances in Fluoroalkylation Strategies: Exploring Novel Reactivities and Synthetic Applications of Sulfone- and Sulfinate-Based Reagents for Mono-, Di-, and Trifluoromethylations
Synthesis,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 5, 2024
Abstract
Fluoroalkylation
serves
as
a
pivotal
strategy
for
chemists
to
precisely
alter
the
properties
of
small
molecules.
Among
established
fluoroalkylation
protocols,
sulfone
and
sulfinate
reagents
stand
out
versatile
tools
these
reactions,
particularly
in
mono-,
di-,
trifluoromethylations.
Their
versatility
lies
offering
multiple
pathways,
encompassing
electrophilic,
nucleophilic,
well
radical
mechanisms,
thus
providing
diverse
routes
controlled
molecular
modifications
through
variety
very
exciting
mechanistic
paths.
1
Introduction
2
Monofluoromethylation
Strategies
2.1
Fluorobis(phenylsulfonyl)methane
(FBSM)
2.2
2-Fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide
(FBDT)
2.3
Benzothiazole-SO2CH2F,
NaSO2CH2F,
ClSO2CH2F
2.4
PhSO2CH2F
3
Difluoromethylation
3.1
PhSO2CF2H
3.2
Benzothiazole-SO2CF2H
3.3
2-PyrSO2CF2H
3.4
NaSO2CF2H
4
Trifluoromethylation
4.1
PhSO2CF3
4.2
2-PyrSO2CF3
4.3
Benzothiazole-SO2CF3
4.4
NaSO2CF3
4.4.1
Electrochemical
Approaches
4.4.2
Photochemical
4.4.3
Other
Noteworthy
5
Conclusion
Язык: Английский