Photoredox-Catalyzed Alkylamination of Alkenes via Oxidative Radical-Polar Crossover and Site-Selective 1,5-Hydrogen Atom Transfer
Organic Letters,
Год журнала:
2024,
Номер
26(32), С. 6847 - 6852
Опубликована: Авг. 7, 2024
We
reported
the
visible-light-mediated
photoredox-catalyzed
oxidative
radical-polar
crossover
and
1,5-hydrogen
atom
transfer
combined
site-selective
remote
C(sp
Язык: Английский
Iron-Catalyzed Three-Component Reactions of Cyclopropanols with Alkenes and N-Heteroarenes via Ring-Opening and C–H Functionalization
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 13, 2025
An
iron-catalyzed
ring-opening
multicomponent
reaction
of
cyclopropyl
alcohols
with
alkenes
and
N-heteroarenes
involving
aryl
C(sp2)-H
functionalization
was
developed.
This
protocol
facilitates
the
regioselective
introduction
both
β-carbonyl
moiety
an
N-heteroarene
group
across
C═C
bond
alkene,
thus
allowing
a
straightforward,
efficient,
facile
access
to
5-heteroarene
ketones.
In
this
process,
strategy
relies
on
alkyl
radical
formation
from
alcohols,
addition
bonds,
heteroaryl
cascades.
general
approach
displays
excellent
selectivity
control
broad
functional-group
tolerance.
Язык: Английский
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
Iron(II)‐Catalyzed 1,2‐Diamination of Styrenes Installing a Terminal NH2 Group Alongside Unprotected Amines
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(45)
Опубликована: Июль 17, 2024
1,2-Diamination
of
alkenes
represents
an
attractive
way
to
generate
differentiated
vicinal
diamines,
which
are
prevalent
motifs
in
biologically
active
compounds
and
catalysts.
However,
existing
methods
usually
limited
scope
produce
diamines
where
one
or
both
nitrogens
protected,
adding
synthetic
steps
for
deprotection
further
N-functionalization
reach
a
desired
target.
Furthermore,
the
range
amino
groups
that
can
be
introduced
at
internal
position
is
fairly
limited.
Here
we
describe
1,2-diamination
styrenes
directly
installs
free
group
terminal
wide
variety
unprotected
nitrogen
nucleophiles
(primary
secondary
alkyl
aromatic
amines,
sulfoximines,
N-heterocycles,
ammonia
surrogate)
position.
Two
complementary
sets
conditions
encompass
electronically
activated
deactivated
with
diverse
substitution
patterns
functional
groups.
Moreover,
this
strategy
extended
1,2-aminothiolation
styrenes.
Язык: Английский
Iron(II)‐Catalyzed 1,2‐Diamination of Styrenes Installing a Terminal NH2 Group Alongside Unprotected Amines
Angewandte Chemie,
Год журнала:
2024,
Номер
136(45)
Опубликована: Июль 17, 2024
Abstract
1,2‐Diamination
of
alkenes
represents
an
attractive
way
to
generate
differentiated
vicinal
diamines,
which
are
prevalent
motifs
in
biologically
active
compounds
and
catalysts.
However,
existing
methods
usually
limited
scope
produce
diamines
where
one
or
both
nitrogens
protected,
adding
synthetic
steps
for
deprotection
further
N‐functionalization
reach
a
desired
target.
Furthermore,
the
range
amino
groups
that
can
be
introduced
at
internal
position
is
fairly
limited.
Here
we
describe
1,2‐diamination
styrenes
directly
installs
free
group
terminal
wide
variety
unprotected
nitrogen
nucleophiles
(primary
secondary
alkyl
aromatic
amines,
sulfoximines,
N
‐heterocycles,
ammonia
surrogate)
position.
Two
complementary
sets
conditions
encompass
electronically
activated
deactivated
with
diverse
substitution
patterns
functional
groups.
Moreover,
this
strategy
extended
1,2‐aminothiolation
styrenes.
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
Remote Radical Azidation of Unactivated C(sp3)–H Bonds in Sulfamoyl Azides
Organic Letters,
Год журнала:
2024,
Номер
26(17), С. 3519 - 3523
Опубликована: Апрель 23, 2024
An
efficient
method
for
remote
radical
C(sp3)–H
azidation
at
unactivated
sites
is
described.
C–H
functionalization
proceeds
via
intramolecular
1,5-hydrogen
atom
transfer
to
N-centered
radicals
that
are
generated
azido
group
and/or
fragmentation.
The
readily
installed
sulfamoyl
azide
serves
as
both
an
amidyl
precursor
and
source.
This
reaction
features
excellent
site
selectivity
tertiary,
secondary,
primary,
benzylic
bonds
exhibits
broad
functional
compatibility.
Язык: Английский