Silylation and (Hetero)aryl/alkenylation of Unactivated Alkenes via Radical-Mediated Distal 1,4-Migration with Hydrosilanes under Organophotocatalysis
Organic Letters,
Год журнала:
2024,
Номер
26(21), С. 4526 - 4531
Опубликована: Май 18, 2024
We
report
a
novel
organic
photoredox
catalysis
to
achieve
unprecedented
γ-(hetero)aryl/alkenyl-δ-silyl
aliphatic
amines
via
silyl-mediated
distal
(hetero)aryl/alkenyl
migration
of
aromatic/alkenyl
bearing
unactivated
alkenes
with
hydrosilanes.
This
protocol
features
mild
and
metal-free
reaction
conditions,
high
atom
economy,
excellent
selectivity,
functional
group
compatibility.
Mechanistic
studies
suggest
that
silylation
(hetero)aryl/alkenylation
involve
hydrogen
transfer
subsequent
1,4-migration
remote
from
nitrogen
carbon.
Язык: Английский
Photocatalytic Three-Component Radical Sulfonarylation of Alkenes: Preparation of γ-Keto-Sulfone-Substituted Oxindoles
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 16, 2025
A
photocatalytic
radical
sulfonarylation
of
N-arylacrylamides
via
a
three-component
cascade
cyclopropyl
alcohol
ring
opening/sulfur
dioxide
insertion/sulfonyl
addition/cyclization
sequence
has
been
developed.
This
method
employs
alcohols
as
the
precursors
β-carbonyl
alkyl
radicals
and
Na2S2O5
cheap
source
sulfur
dioxide.
By
using
this
procedure,
wide
variety
γ-keto-sulfone-substituted
oxindoles
were
facilely
synthesized.
Язык: Английский
Three-Component Reaction of Cyclopropanols, DABSO, and N-(Sulfonyl)acrylamides: Preparation of Sulfone-Bridged 1,7-Dicarbonyl Compounds
Organic Letters,
Год журнала:
2024,
Номер
26(34), С. 7170 - 7175
Опубликована: Авг. 19, 2024
A
cascade
reaction
of
cyclopropyl
alcohols,
DABSO
(1,4-diazoniabicyclo[2.2.2]octane-1,4-disulfinate),
and
N-(sulfonyl)acrylamides
has
been
developed.
This
tandem
process
went
through
a
cyclopropanol
ring
opening
Michael
addition
sequence.
The
γ-keto
sulfinate
generated
from
the
between
serves
as
nucleophilic
reagent,
N-(sulfonyl)acrylamide
is
used
acceptor.
By
utilizing
this
strategy,
multitudinous
sulfone-bridged
1,7-dicarbonyl
compounds
that
contain
both
β-sulfonyl
amide
unit
sulfone
skeleton
were
conveniently
synthesized.
Язык: Английский
Stable and Recyclable Copper Nanoclusters with Exposed Active Sites for Broad‐Scope Protosilylation in Open Air
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 25, 2024
Abstract
Despite
recent
advances
in
cluster‐based
catalysis
for
organic
synthesis,
the
substrate
scope
of
reactions
catalyzed
by
metal
nanoclusters
is
typically
not
superior
to
previously
established
catalytic
systems.
Herein,
we
develop
new
atomically
precise
copper
protosilylation,
with
expanding
alkenes
and
simple
enynes
that
were
suitable
prior
synthetic
methodologies
traditional
complexes.
The
involvement
a
second
center
kernel
during
migratory
insertion
step
thought
be
responsible
expanded
scope.
In
addition,
reaction
highly
compatible
water
can
carried
out
open
air
rather
than
under
inert
gas
protection.
Mechanistic
studies
suggest
cluster‐catalyzed
protosilylation
proceeds
absence
silyl
radicals.
current
findings
demonstrate
potential
using
practical
sustainable
chemical
synthesis.
Язык: Английский
Organic Photoredox-Catalyzed Hydrosilylation of Vinylboronic Esters for the Synthesis of Geminal and Vicinal Borosilanes
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(22), С. 16463 - 16472
Опубликована: Окт. 24, 2024
Geminal
and
vicinal
borosilanes
have
unique
applications
in
functional
materials
synthetic
transformations.
Herein,
a
convenient
method
for
the
synthesis
of
geminal
is
developed
via
photoredox
metal-free
hydrosilylation
vinylboronic
esters.
This
strategy
features
advantages
high
atom
economy,
environmental
friendliness,
excellent
group
compatibility.
The
mechanism
studies
reveal
that
catalytic
reaction
goes
through
HAT
catalysis
radical
addition
pathway.
Язык: Английский
Silyl Radical‐Participated Silylfunctionalization of Alkenes and Alkynes
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 1, 2024
Abstract
Alkenes
and
alkynes
are
inexpensive
readily
available
basic
chemicals.
Silyl
radical‐participated
silylation
of
alkenes
provides
a
powerful
tool
for
the
direct
construction
organosilicon
compounds.
Compared
to
hydrosilylation
reactions,
silylfunctionalization
reactions
more
attractive
advantageous
in
building
diverse
compounds,
which
has
led
their
becoming
research
focus
organic
synthesis.
Herein,
we
provide
comprehensive
overview
recent
advances
silyl
alkynes.
Язык: Английский
Stable and Recyclable Copper Nanoclusters with Exposed Active Sites for Broad‐Scope Protosilylation in Open Air
Angewandte Chemie,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 25, 2024
Abstract
Despite
recent
advances
in
cluster‐based
catalysis
for
organic
synthesis,
the
substrate
scope
of
reactions
catalyzed
by
metal
nanoclusters
is
typically
not
superior
to
previously
established
catalytic
systems.
Herein,
we
develop
new
atomically
precise
copper
protosilylation,
with
expanding
alkenes
and
simple
enynes
that
were
suitable
prior
synthetic
methodologies
traditional
complexes.
The
involvement
a
second
center
kernel
during
migratory
insertion
step
thought
be
responsible
expanded
scope.
In
addition,
reaction
highly
compatible
water
can
carried
out
open
air
rather
than
under
inert
gas
protection.
Mechanistic
studies
suggest
cluster‐catalyzed
protosilylation
proceeds
absence
silyl
radicals.
current
findings
demonstrate
potential
using
practical
sustainable
chemical
synthesis.
Язык: Английский
Synthesis of succinyldiamides containing all-quaternary carbon center by photo-induced amidation/smiles rearrangement of alkenes
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 23, 2024
A
novel,
mild,
and
environmentally
friendly
method
was
developed
for
the
synthesis
of
quaternary-carbon-containing
succinyldiamides.
This
found
to
be
compatible
with
many
substrates.
Язык: Английский