Hydrogen-Bonding Network-Enabled Terminal Selective Heteroarylation of Allenamides in Hexafluoroisopropanol
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 21, 2025
Hexafluoroisopropanol
(HFIP)-mediated
terminal
selective
heteroarylation
of
allenamides
has
been
accomplished
through
H-bonding
network-enabled
substrate
activation
in
a
robust
fashion.
This
strategy
features
cascade
process
involving
sequential
nucleophilic
addition
followed
by
electrophilic
heteroaromatic
substitution
and
is
well
suited
for
late-stage
functionalization
complex
bioactive
molecules.
The
elucidation
the
underlying
mechanism
was
achieved
comprehensive
combination
several
control
experiments,
kinetic
studies,
isotopic
labeling
isolation
HFIP-allenamide
intermediate
adduct.
Язык: Английский
HFIP-Mediated Cascade Aminomethylation and Intramolecular Cyclization of Allenamides with N,O-Acetals to Access Tetrahydro-β-carboline Derivatives
Chemical Communications,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
A
cascade
of
two
C–C
bond
forming
reactions
promoted
alone
by
HFIP
is
described
delivering
tetrahydro-β-carboline
derivatives
embedded
with
an
allylic
amine
functionality.
Язык: Английский
Hexafluoroisopropanol (HFIP)-Mediated Intramolecular Cyclization of Allenamides To Access C1-Vinyl Tetrahydro-β-carbolines
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(16), С. 11783 - 11788
Опубликована: Июль 26, 2024
The
construction
of
biologically
interesting
N-heterocycles
under
metal-free
conditions
is
a
constant
goal
in
industry
and
academia.
Herein,
we
have
developed
an
hexafluoroisopropanol
(HFIP)-mediated
intramolecular
cyclization
allenamides,
providing
tetrahydro-β-carboline
derivatives
embedded
with
C1-vinyl
functionality.
protocol
provided
atom-efficiently
room
temperature
broad
substrate
scope
good
to
excellent
yields.
potential
impact
the
further
highlighted
by
synthesizing
important
molecules
diversified
scaffolds
via
postsynthetic
modifications.
Язык: Английский