Hydrogen-Bonding Network-Enabled Terminal Selective Heteroarylation of Allenamides in Hexafluoroisopropanol
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 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.
Language: Английский
Lewis acid‐promoted C–H Chalcogenation of Arenes and Heteroarenes
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 16, 2024
Abstract
An
efficient
catalytic
system
employing
TMS•OTf
for
the
regioselective
thiolation
of
electron‐rich
arenes
with
sulfonyl
hydrazides
has
been
developed.
The
reaction
occurs
in
a
solvent
mixture
dichloroethane
and
trifluoroethanol
under
mild
conditions,
addition
water.
This
method
furnishes
range
para
‐thio‐substituted
3‐sulfenyl‐indoles
good
to
excellent
yields,
marking
significant
advancement
organic
synthesis.
Language: Английский