ACS Catalysis,
Год журнала:
2021,
Номер
11(21), С. 13363 - 13373
Опубликована: Окт. 19, 2021
Reactions
involving
allenyl
ion
intermediates
have
been
widely
applied
in
the
synthesis
of
functionalized
allenes,
but
reactions
radicals
less
studied
and
limited
successful
examples
realized
mainly
by
transition
metal
catalysis.
We
herein
demonstrate
generation
N-heterocyclic
carbene
(NHC)
organocatalysis
their
applications
three-component
radical
relay
1,4-alkylcarbonylation
1,3-enynes
without
participation.
This
strategy
could
accommodate
a
collection
different
alkyl
precursors
such
as
CF3I,
halides,
cycloketone
oxime
esters,
aliphatic
carboxylic
acid
derived
redox-active
enabling
convenient
pathway
to
access
range
synthetically
challenging
tetra-substituted
ketones
with
high
regioselectivity.
The
key
success
this
protocol
relied
on
Csp-C(O)sp2
radical–radical
coupling
NHC-bound
ketyl
radicals,
constructing
ketone
motifs
highly
efficient
reaction
pathway.
Chinese Journal of Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 19, 2025
Comprehensive
Summary
A
novel
and
efficient
method
for
selective
synthesis
of
bromo‐substituted
2
H
‐pyrroles
3
has
been
achieved
from
1,3‐enynes,
NBS
TMSN
via
O‐promoted
cyclization
reactions
or
TFA‐catalyzed
cyclization/2,3‐shift
reactions,
providing
a
range
structurally
diverse
products
in
moderate
to
good
yields
under
mild
conditions.
The
Tf2O-promoted
cascade
cyclization
of
2-benzoylbenzoic
acids
with
arylalkynes
was
achieved
under
solvent-free
ball-milling
conditions.
This
process
renders
rapid
entry
to
the
rare
indene-containing
spirolactones
via
intramolecular
and
subsequent
annulation
arylalkynes,
which
resulted
in
one
C-O
two
C-C
bond
formations.
As
reactions
utilize
easily
available
starting
materials
proceed
absence
organic
solvents,
present
protocol
constitutes
an
expedient
environmentally
friendly
access
spirolactones.
Organic Letters,
Год журнала:
2021,
Номер
23(21), С. 8510 - 8515
Опубликована: Окт. 15, 2021
Presented
herein
is
an
efficient
and
unprecedented
synthesis
of
indolyl-tethered
spiro[cyclobutane-1,1'-indenes]
through
the
cascade
reaction
1-(pyridin-2-yl)-1H-indoles
with
alkynyl
cyclobutanols.
Mechanistic
experiments
implicate
a
sequential
process
in
which
1-(pyridin-2-yl)-1H-indole
first
undergoes
alkenylation
cyclobutanol
followed
by
intramolecular
Friedel-Crafts
to
give
title
products.
The
utility
this
novel
protocol
was
reflected
ample
substrate
scope,
high
chemo-
regioselectivity,
removable
directing
group,
scalable
preparation.
In
addition,
product
thus
obtained
can
be
further
derivatized
quite
efficiently.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(21), С. 4385 - 4390
Опубликована: Янв. 1, 2022
A
metal-free
three-component
protocol
for
quinoline
synthesis
is
developed
by
using
alkyl
lactates,
anilines
and
α-keto
acids.
In
vitro
experiments
disclose
the
attractive
anti-inflammatory
activity
of
these
compounds.
Organic Letters,
Год журнала:
2023,
Номер
25(48), С. 8547 - 8552
Опубликована: Ноя. 29, 2023
Phosphine-catalyzed
cascade
isomerization/annulation
has
been
developed
to
realize
a
diastereoselective
synthesis
of
allenes
installed
on
the
hexahydropentalene
skeleton,
which
contains
five
chiral
centers
(and
one
axial
chirality).
This
reaction
tolerated
broad
range
allenoates
and
enynes.
The
allene
products
were
transformed
various
halogen-substituted
fused-ring
compounds.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(5), С. 1410 - 1416
Опубликована: Янв. 1, 2022
Presented
herein
is
a
novel
synthesis
of
spirocyclopropylpyrazoles
tethered
with
trifluoromethyl
unit
through
an
unprecedented
cascade
reaction
alkylidenecyclopropanes
pyrazolidinones
and
trifluoroethanol.
RSC Advances,
Год журнала:
2022,
Номер
12(37), С. 24237 - 24241
Опубликована: Янв. 1, 2022
An
efficient
approach
to
divergently
access
γ-hydroxy-butenolides
and
γ-alkylidene-butenolides
via
annulation
reaction
of
α-keto
acids
with
simple
aliphatic
ketones
is
reported
herein.
