Alkyl radicals from diacyl peroxides: metal-/base-/additive-free photocatalytic alkylation of N-heteroaromatics
Green Chemistry,
Год журнала:
2023,
Номер
25(20), С. 7971 - 7977
Опубликована: Янв. 1, 2023
Alkyl
diacyl
peroxides
were
demonstrated
to
be
efficient
alkylating
reagents
for
the
visible-light-induced
4CzIPN-catalyzed
direct
C–H
alkylation
of
N
-heteroaromatics.
Язык: Английский
Recent Advances in Cyclization Reactions of 1,6‐Enynes
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(6), С. 1220 - 1268
Опубликована: Янв. 22, 2024
Abstract
Elaborated
molecular
architectures,
specifically
those
bearing
one
or
more
carbon
stereocenters,
stand
as
an
important
class
of
carbocyclic
and
heterocyclic
frameworks
because
they
are
frequently
occurring
core
structures
in
numerous
natural
products
biologically
active
pharmaceutical
molecules.
Over
the
past
few
decades,
development
versatile
synthetic
approaches
via
cascade
cyclization
reactions
1,6‐enynes
for
construction
a
series
fused
spiro
compounds
has
been
focus
great
deal
research
initiatives.
These
synthesis
strategies
peculiarly
fascinating
context
assembly
wide
array
molecules,
products,
agrochemicals,
functional
materials.
In
this
review,
recent
developments
transformations
with
diverse
coupling
reagents
summarized
since
2018,
which
could
be
divided
into
five
categories:
1)
Introduction;
2)
Transition
metal
catalyzed
1,6‐enynes;
3)
Metal‐free
4)
Visible‐light‐induced
5)
Electrocatalytic
1,6‐enynes.
Язык: Английский
Base-Promoted Regioselective Annulation of Pyridinium Ylides and Bromoalkynes for the Chemodivergent Synthesis of Indolizines
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 5, 2025
A
base-promoted
regioselective
formal
[3
+
2]
annulation
of
pyridinium
ylides
with
bromoalkynes
is
reported,
producing
a
series
substituent-diverse
indolizines
in
generally
good
yields.
mild
K2CO3-promoted
three-component
cyclization
and
at
2:1
molar
ratio
delivered
C2-acylmethylated
indolizines,
whereas
C2-brominated
were
generated
starting
from
bearing
strong
electron-withdrawing
groups
the
unit
by
using
2,2,6,6-tetramethyl-1-piperidinyloxy
as
dehydrogenating
reagent.
The
current
synthetic
methodology
offers
controllable
modular
approach
to
access
different
substitution
patterns,
featuring
wide
substrate
scope,
functional
group
compatibility,
complete
regioselectivity
without
demand
any
transition-metal
catalysts.
Язык: Английский
Photocatalytic Multicomponent Annulation of Amide-Anchored 1,7-Diynes Enabled by Deconstruction of Bromotrichloromethane
Daixiang Chen,
Yu Bao,
Shenghu Yan
и другие.
Molecules,
Год журнала:
2024,
Номер
29(4), С. 782 - 782
Опубликована: Фев. 8, 2024
We
present
the
first
example
of
visible-light-mediated
multicomponent
annulation
1,7-diynes
by
taking
advantage
quadruple
cleavage
olf
carbon-halogen
bonds
BrCCl3
to
generate
a
C1
synthon,
which
was
adeptly
applied
preparation
skeletally
diverse
3-benzoyl-quinolin-2(1H)-one
acetates
in
moderate
good
yields.
Controlled
experiments
demonstrated
that
H2O
acted
as
both
oxygen
and
hydrogen
sources,
gem-dichlorovinyl
carbonyl
compound
exhibited
critical
intermediate
this
process.
The
mechanistic
pathway
involves
Kharasch-type
addition/6-exo-dig
cyclization/1,5-(SN”)-substitution/elimination/binucleophilic
1,6-addition/proton
transfer/tautomerization
sequence.
Язык: Английский
Metal-Free Synthesis of 2H-Indazole Skeletons by Photochemistry or Thermochemistry
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(17), С. 12341 - 12356
Опубликована: Авг. 15, 2023
A
simple
and
tuned
synthesis
of
a
2H-indazole
skeleton
under
metal-free
conditions
was
developed.
Under
visible-light
irradiation
at
room
temperature,
2-((aryl/alkyl/H)ethynyl))aryltriazenes
reacted
with
arylsulfinic
acids
to
afford
3-functionalized
2H-indazoles
without
extra
photocatalyst
via
an
electron
donor-acceptor
complex.
In
the
presence
acid,
2-(ethynyl)aryltriazenes
underwent
intramolecular
oxidation/cyclization
provide
2H-indazole-3-carbaldehydes
50
°C
in
air.
Язык: Английский
Visible-Light-Mediated Radical Hydroalkylative Cyclization of 1,6-Enynes
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(23), С. 16639 - 16643
Опубликована: Ноя. 17, 2023
A
radical
hydroalkylative
cyclization
approach
accessing
various
alkenyl
heterocyclic
compounds
was
developed
using
dimethyl
malonate
and
1,6-enynes
in
the
presence
of
visible-light
photoredox
catalysis.
The
use
Ir(dtbbpy)(ppy)2PF6
as
a
photosensitizer
enables
carbon
atom
formation
initiates
cascade
reaction
under
mild
conditions.
Язык: Английский
Visible Light-promoted Preparation of 2,3-Dihydrobenzofurans and Coumaranones
Current Organic Chemistry,
Год журнала:
2024,
Номер
28(11), С. 830 - 843
Опубликована: Апрель 25, 2024
Abstract:
2,3-Dihydrobenzofuran
and
coumaranone
are
readily
available
in
numerous
naturally
occurring
compounds.
They
mostly
exist
plenty
of
food
plants
medicinal
plants.
Such
compounds
constitute
a
series
flavor
components
bioactive
molecules.
Their
preparation
has
been
an
attractive
field
research.
In
the
past
few
decades,
great
efforts
have
made
2,3-dihydrobenzofuran
structure
through
both
metal-catalyzed
organocatalyzed
ways.
Visible
light-promoted
reactions
sprang
up
early
21st
century
represent
green
manner
transformations.
Under
irradiation
visible
light,
radicals
could
be
generated
under
milder
conditions.
Thus,
lightpromoted
spread
widely
chemical
synthesis.
recent
years,
developed
by
different
groups,
including
intramolecular
intermolecular
reactions.
The
benign
reaction
conditions
allow
better
functional
group-tolerance
lead
to
diverse
structures.
Several
reviews
on
synthesis
2,3-
dihydrobenzofuran
reported.
However,
approaches
such
structures
not
well
reviewed.
Our
review
will
cover
literature
that
reported
discovery
2,3-dihydrobenzofuran,
attempting
summarize
existing
methods
provide
guidance
chemists
present
challenges.
Язык: Английский