Synlett,
Journal Year:
2022,
Volume and Issue:
33(09), P. 822 - 835
Published: Jan. 25, 2022
Abstract
This
Account
summarizes
the
research
of
group
on
multicomponent
reactions
arena
with
fundamental
heterocycles
as
substrates,
using
mechanistic
considerations
to
hypothesize
new
processes
and
rationalize
results.
Biomedical
applications
ensuing
adducts
were
also
envisaged,
which
brought
about
interesting
discoveries.
1
Introduction
Context
2
The
Beginnings:
Unexplored
Heterocyclic
Substrates
3
Interrupted
Processes
4
Multiple
Multicomponent
Reactions:
Problem
Selectivity
5
Extended
Reactions
6
Conclusions
Wishes
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 12, 2024
We
herein
report
the
serendipitous
discovery
of
interrupted
Plancher
rearrangement
initiated
by
an
HFIP-promoted
dearomative
epoxide-indole
cyclization,
unlocking
a
new
blueprint
to
formal
C3
umpolung
reactivity
indoles.
This
rapid
complexity
generating
cascade
process
paves
way
toward
class
fused-bridged
indolines
in
high
yields
and
under
full
regio-
diastereocontrol.
The
reaction
is
amenable
wide
range
substituents
starting
materials.
The
photoactivation
of
electron
donor-acceptor
(EDA)
complexes
has
emerged
as
a
sustainable,
selective
and
versa-tile
strategy
for
the
generation
radical
species.
However,
when
it
comes
to
aryl
formation,
this
remains
hamstrung
by
electronic
properties
aromatic
precursors
electron-deficient
halide
acceptors
are
required.
This
prevented
implementation
general
synthetic
platform
for-mation.
Our
study
introduces
triarylsulfonium
salts
in
photoactive
EDA-complexes,
used
combina-tion
with
catalytic
amounts
newly-designed
amine
donors.
sulfonium
salt
label
renders
inconsequential
features
precursor
and,
more
importantly,
is
installed
regioselectively
native
aro-matic
compounds
C–H
sulfenylation.
Using
general,
site-selective
functionalization
approach,
we
have
developed
metal-free
protocols
alkylation
cyanation
arenes,
showcased
their
application
both
synthesis
late-stage
modification
pharmaceuticals
agrochemicals.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(50), P. 9053 - 9057
Published: Dec. 12, 2023
A
palladium-catalyzed
domino
reaction
of
alkene-tethered
oxime
esters
is
reported.
This
transformation
uses
an
air-stable
palladium
precatalyst
that
initiates
a
Narasaka-Heck
reaction,
interrupted
with
Pd(II)-promoted
cyclization.
Through
this
methodology,
novel
class
unsymmetrical
alkyl-linked
bis-heterocycles
were
synthesized
in
yields
up
to
99%.
The
scalable
1.0
mmol,
simplified
purification
steps.
expands
the
scope
accessible
available
through
reactions
beyond
C-H
activation
and
direct
anionic
capture
termination
European Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
2022(6)
Published: Jan. 21, 2022
Abstract
An
unusual
reactivity
of
the
α,α‐diiodo‐α’‐acetoxyketones
with
o
‐phenylenediamines
is
reported
through
formation
2‐arylbenzimidazoles.
A
systematic
study
a
series
fruitful
control
experiments
and
isolation
key
intermediates
unravelled
unprecedented
domino
mechanism.
This
process
involves
stepwise
two‐carbon
fragmentation
pathway
sequential
amidation–aziridination–decarbonylation–I
2
‐mediated
aminative
cyclization–oxidation
reactions.
strategy
employs
no
additives
like
oxidant,
metal
catalyst,
bases,
represents
yet
another
novel
profile
building
blocks
α,α‐diiodo‐α’‐acetoxyketones.
Synlett,
Journal Year:
2022,
Volume and Issue:
33(09), P. 822 - 835
Published: Jan. 25, 2022
Abstract
This
Account
summarizes
the
research
of
group
on
multicomponent
reactions
arena
with
fundamental
heterocycles
as
substrates,
using
mechanistic
considerations
to
hypothesize
new
processes
and
rationalize
results.
Biomedical
applications
ensuing
adducts
were
also
envisaged,
which
brought
about
interesting
discoveries.
1
Introduction
Context
2
The
Beginnings:
Unexplored
Heterocyclic
Substrates
3
Interrupted
Processes
4
Multiple
Multicomponent
Reactions:
Problem
Selectivity
5
Extended
Reactions
6
Conclusions
Wishes
