Condition-Controlled Divergent Selective Synthesis of (Z)-N-Vinyl and N-Allenyl Benzimidazoles by Pd- or Bi-Catalyzed Direct N-Alkenylation Reactions
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 6, 2025
We
have
developed
a
condition-controlled
divergent
synthesis
of
(Z)-N-vinyl
and
N-allenyl
benzimidazoles
from
1,1,3-triphenylprop-2-yn-1-ols
through
Pd-
or
Bi-catalyzed
N-alkenylation
reactions
involving
nucleophilic
attack
C-C
bond
cleavage
processes.
The
desired
two
different
kinds
products
can
be
conveniently
selectively
synthesized
by
using
this
strategy,
which
features
stereospecific
synthesis,
good
functional
group
tolerance,
broad
substrate
scope,
high
efficiency.
strategy
provides
significant
advantages
for
the
biologically
pharmaceutically
active
imidazoheterocycles.
Язык: Английский
Transformation of Sulfoximines and Cyclic Sulfoximines
Опубликована: Янв. 1, 2025
Язык: Английский
gem-Difluoroallene (DFA): An Emerging Versatile Synthetic Precursor to Enable Diverse Fluorinated Molecules
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
Organofluorine
compounds
are
increasingly
found
in
diverse
fields,
such
as
pharmaceuticals,
agrochemicals,
and
materials
science.
Язык: Английский
Palladium(II)-Catalyzed Regioselective Hydroamination of Allylamines to N-Alkyl Sulfoximines
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 14, 2025
An
intermolecular
coupling
between
sulfoximines
and
allyl
amines,
linked
to
the
picolinamide
directing
group,
is
developed
by
leveraging
a
nucleopalladation-guided
regioselective
hydroamination
strategy,
enabling
production
of
range
valuable
N-alkyl
in
high
yields.
The
protocol
features
operational
simplicity
broad
substrate
scope
was
also
amenable
aniline
nucleophiles.
Synthetic
utilities
were
showcased
through
scale-up
reactions
product
diversifications,
leading
biorelevant
molecules.
Язык: Английский
Palladium-Catalyzed Regio- and Enantioselective Hydrophosphination of gem-Difluoroallenes
Organic Letters,
Год журнала:
2023,
Номер
25(32), С. 5957 - 5962
Опубликована: Авг. 10, 2023
Chiral
allylic
phosphines
and
gem-difluoroalkenes
are
both
important
structural
motifs
in
various
bioactive
molecules,
chiral
ligands,
natural
products.
These
two
now
integrated,
we
herein
report
a
straightforward
atom-economical
enantioselective
hydrophosphination
of
gem-difluoroallenes
using
disubstituted
phosphines.
A
wide
array
enantioenriched
fluorinated
has
been
accessed
with
excellent
regio-
enantioselectivity
high
efficiency.
Synthetic
catalytic
applications
phosphine
products
have
demonstrated.
Язык: Английский
Copper-Catalyzed Protoarylation of gem-Difluoroallenes
Organic Letters,
Год журнала:
2024,
Номер
26(2), С. 525 - 529
Опубликована: Янв. 5, 2024
A
copper-catalyzed
protoarylation
of
gem-difluoroallenes
with
aryl
boronic
esters
has
been
developed,
enabling
highly
regioselective
synthesis
gem-difluoroalkenes
in
high
yields.
The
mild
reaction
conditions
allow
for
a
variety
functional
groups
to
be
tolerated,
and
the
can
extended
protoalkenylation
gem-difluoroallenes.
synthetic
utility
this
method
demonstrated
gram-scale
operation
as
well
chiral
bearing
γ-carbon
stereogenic
centers
moderate
enantioselectivity
using
bidentate
phosphine
ligand
copper
catalyst.
Язык: Английский
Alkylation of NH-sulfoximines under Mitsunobu-type conditions
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(25), С. 5181 - 5184
Опубликована: Янв. 1, 2023
Previously
described
approaches
for
the
alkylation
of
NH-sulfoximines
typically
rely
either
on
transition
metal
catalysis,
or
use
traditional
reagents
and
strong
bases.
Herein,
we
report
a
straightforward
diverse
under
simple
Mitsunobu-type
conditions,
despite
unusually
high
pKa
NH
center.
Язык: Английский
Organoboron/Palladium Cocatalytic Allylation of NH-Sulfoximines Using Allylic Alcohols
Organic Letters,
Год журнала:
2023,
Номер
25(46), С. 8274 - 8278
Опубликована: Ноя. 14, 2023
Synergistic
organoboron/palladium
cocatalysis
enables
dehydrative
couplings
of
NH-sulfoximines
with
allylic
alcohols,
furnishing
the
corresponding
N-allylated
products.
The
reactions
proceed
in
absence
a
Brønsted
base
and
are
tolerant
diverse
sulfoximine
partners,
including
functionalized
variants.
Experimental
computational
studies
suggest
that
reagent
is
activated
by
complexation
to
boronic
acid
cocatalyst.
Язык: Английский
Z-Selective access to α-trifluoromethyl arylenes through Pd-catalysed fluoroarylation of 1,1-difluoroallenes
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(45), С. 8979 - 8983
Опубликована: Янв. 1, 2023
The
synthesis
of
stereo-defined
α-trifluoromethyl
arylenes
is
great
importance
in
medical
chemistry,
organic
and
materials
science.
However,
despite
the
recent
advances,
Z-selective
formation
has
remained
underdeveloped.
Here,
we
describe
a
facile
approach
towards
Z-α-trifluoromethyl
through
Pd-catalysed
stereoselective
fluoroarylation
1,1-difluoroallenes
presence
bulky
monophosphine
ligand.
Язык: Английский