Direct Fluorosulfonamidation of (Hetero)arenes and Alkenes with Photoredox-Active Fluorosulfamoyl Radical Reagents
ACS Catalysis,
Год журнала:
2024,
Номер
14(16), С. 12082 - 12092
Опубликована: Июль 29, 2024
Sulfur(VI)
fluoride
exchange
(SuFEx)
is
a
second-generation
click
chemistry
reaction
that
relies
on
the
unique
reactivities
of
SVI–F
bonds.
The
development
efficient
methods
for
incorporating
S(VI)–F
motif
into
molecules
great
significance.
Sulfamoyl
fluorides
(R1R2NSO2F),
serving
as
versatile
SuFExable
hubs,
are
typically
synthesized
by
using
"+SO2F"
reagents
to
establish
N-SO2F
In
this
study,
we
report
N-fluorosulfamoyl
pyridium
salts
(NFSAPs)
radical
fluorosulfonamidation
readily
accessible
and
bench-stable.
By
employing
NFSAPs
essential
fluorosulfamoyl
(•NSO2F)
precursors,
direct
installation
NSO2F
group
onto
(hetero)arenes
alkenes
achieved
through
distinct
C–N
bond
formation
reactions.
This
platform
facilitates
collective
synthesis
highly
functionalized
N-aryl,
N-alkyl,
N-alkenyl
sulfamoyl
(R1R2NSO2F)
under
mild
photocatalytic
conditions
has
been
applied
in
late-stage
functionalization
pharmaceuticals
peptides.
Язык: Английский
Photocatalyzed Acylmethylation/Cyclization of Unactivated Alkenes with Sulfoxonium Ylides towards Acylmethylated Polycyclic Quinazolinones
ChemCatChem,
Год журнала:
2024,
Номер
unknown
Опубликована: Май 16, 2024
Abstract
The
synthesis
of
acylmethylatated
pyrrolo‐quinazolinones
was
developed
via
photo‐induced
cascade
radical
addition/cyclization
N
‐(but‐3‐enyl)quinazolin‐4(3
H
)‐ones
with
sulfoxonium
ylides
using
4CzIPN
as
the
photocatalyst.
This
approach
also
suitable
for
construction
piperidino‐quinazolinones.
protocol
features
mild
conditions,
convenient
operation,
broad
substrate
scope
and
good
functional
group
compatibility.
Язык: Английский
Advances in C‐N bond Formation via N‐centered Radicals from N‐Aminopyridinium Reagents
Farrukh Sajjad,
Chang Lu,
Tie–Gen Chen
и другие.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 12, 2024
Abstract
Nitrogen‐centered
radicals
(NCRs)
have
gained
significant
attention
due
to
their
high
reactivity,
which
facilitates
many
useful
and
challenging
transformations,
particularly
in
the
formation
of
C−N
bonds.
In
this
regard,
N
‐aminopridinium
reagents
are
easily
accessible
substrates
that
readily
generate
‐centered
radicals,
can
be
trapped
by
arenes,
olefins,
alkynes
even
alkanes
under
visible
light
irradiation.
recent
years,
amination
strategies
involving
‐aminopyridinium
salts
grown
remarkably
attracted
considerable
interest
within
synthetic
community.
This
review
comprehensively
includes
all
advances
bond
construction
via
derived
from
substrates.
Язык: Английский
Electrochemical Oxidative Cascade Cyclization of Alkenyl Alcohols with External Nucleophiles to Access Amino- and Hydroxy-Functionalized O-Heterocycles
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 20, 2024
A
convenient
electrochemical
oxidative
cascade
cyclization
of
alkenes
equipped
with
pendant
alcohols
general
nucleophiles
was
developed.
Using
readily
available
diarylmethanimine
and
carboxylic
acids
as
nucleophilic
sources,
a
broad
range
internal
alkene
terminal
substrates
could
produce
RCO2-
Ar2CN-functionalized
O-heterocycles
in
moderate
to
high
yields
without
the
requirement
for
external
oxidants
metals.
These
resulting
products
can
subsequently
be
hydrolyzed
yield
valuable
NH2-
OH-functionalized
tetrahydrofurans
tetrahydropyranes
under
mild
conditions.
Importantly,
efficient
conversion
secondary
alcohol
amines
complete
inversion
configuration
enhances
methodology,
enabling
construction
2-aryl-3-amino
tetrahydrofuran
complementary
diastereoselectivity.
Язык: Английский