Handbook of CH‐Functionalization,
Journal Year:
2022,
Volume and Issue:
unknown, P. 1 - 48
Published: Oct. 1, 2022
Abstract
Transition
metal‐catalyzed
transformations
involving
converting
CH
bonds
into
CC
or
CX
bond
have
been
extensively
explored,
which
expedite
the
synthesis
of
target
molecules
via
novel
and
efficient
disconnections
in
retrosynthetic
analysis.
Directing
group‐assisted
activation
is
one
most
used
strategy
to
obtain
site‐selective
functionalization.
Ideal
directing
groups
are
ubiquitously
available,
stable,
easily
removed,
transformable.
Carboxylates
perfectly
meet
with
those
prerequisites.
Carboxylic
acids
widely
exist
organic
molecules,
can
be
tracelessly
removed
by
protodecarboxylation
converted
other
functional
groups.
Thus,
carboxylate‐directed
significant
importance.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(29), P. 5260 - 5265
Published: July 15, 2022
An
efficient
ruthenium(II)-catalyzed
tandem
C-C/C-N
bond
formation
with
aryl
amides
and
7-azabenzonorbornadienes
has
been
developed
to
synthesize
cis-fused
dihydrobenzo[c]phenanthridinones.
The
amide
group
functions
as
a
directing
well
leaving
provides
an
easy
access
the
pharmaceutically
useful
benzo[c]phenanthridine
alkaloids
such
nitidine
fagaronine
analogues.
present
methodology
is
compatible
various
functional
groups
respect
azabicyclic
alkenes
aromatic
amides.
reaction
mechanism
involving
directing-group-assisted
C-H
activation
was
proposed
supported
by
deuterium
labeling
studies.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(25), P. 5159 - 5169
Published: Jan. 1, 2024
An
Ru-catalyzed
carbamoyl-directed
C–H
functionalization
of
indoles
and
indolines
with
7-azabenzonorbornadienes
results
in
2-aminodihydronaphthyl
7-aminodihydronaphthyl
indolines,
respectively.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
63(1)
Published: Nov. 9, 2023
A
PdII
-catalyzed,
domino
enantioselective
desymmetrizative
coupling
of
7-azabenzonorbornadienes
with
alkynylanilines
is
disclosed
herein.
This
operationally
simple
transformation
generates
three
covalent
bonds
and
two
contiguous
stereocenters
excellent
enantio-
diastereo-selectivity.
The
resulting
functionalized
indole-dihydronaphthalene-amine
conjugates
served
as
an
appealing
platform
to
streamline
the
diversity-oriented
synthesis
(DOS)
other
valuable
enantioenriched
compounds.
DFT
calculations
revealed
that
stabilizing
non-covalent
interactions
contributed
observed
enantioselectivity.
Molecules,
Journal Year:
2023,
Volume and Issue:
28(8), P. 3508 - 3508
Published: April 16, 2023
A
microwave-promoted
multicomponent
reaction
of
isatins,
α-amino
acids
and
1,4-dihydro-1,4-epoxynaphthalene
is
achieved
under
environmentally
friendly
conditions,
delivering
oxygen-bridged
spirooxindoles
within
15
min
in
good
to
excellent
yields.
The
attractive
features
the
1,3-dipolar
cycloaddition
are
compatibility
various
primary
amino
high
efficiency
short
time.
Moreover,
scale-up
synthetic
transformations
spiropyrrolidine
oxindole
further
demonstrate
its
utility.
This
work
provides
powerful
means
expand
structural
diversity
spirooxindole
as
a
promising
scaffold
for
novel
drug
discovery.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(21), P. 3853 - 3858
Published: May 18, 2023
An
efficient
synthesis
of
benzo[c]phenanthridine
alkaloids
via
a
synergistic
combination
C-C
bond
formation
and
cycloaromatization
reaction
is
described.
Aryl
nitrones
react
with
7-azabenzonorbornadienes
in
the
presence
Rh(III)
catalyst,
providing
pharmaceutically
useful
derivatives
good
to
moderate
yields.
Using
this
methodology,
highly
such
as
norfagaronine,
norchelerythrine,
decarine,
norsanguinarine,
nornitidine
were
prepared
single
step.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(21), P. 14826 - 14843
Published: Sept. 28, 2021
The
biologically
important
naturally
available
benzophenanthridines
were
prepared
efficiently
in
three
steps
with
overall
good
yields.
A
new
synthetic
methodology
involving
a
rhodium(III)
catalyzed
redox-neutral
ring-opening
of
7-azabenzonorbornadienes
aromatic
aldoximes
is
developed
to
synthesize
the
target
molecules.
C–H
reaction
highly
diastereoselective
and
compatible
various
sensitive
functional
group
substituted
as
well
7-azabenzonorbornadienes.
products
transformed
into
13,14-dehydrobenzo
phenanthridine
derivatives
by
HCl
hydrolysis.
Subsequently,
13,14-dehydrobenzophenanthridines
converted
benzophenanthridine
alkaloids
presence
DDQ.
possible
mechanism
was
proposed
for
supported
deuterium
labeling
studies.
Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
363(5), P. 1346 - 1351
Published: Jan. 19, 2021
Abstract
A
catalyst
and
additive‐free
strategy
for
selective
ring‐opening
selenocyanation
of
saturated
heterocycles
with
elemental
selenium
TMSCN
is
developed,
affording
a
series
aliphatic
selenocyanates
selenaheterocycles.
In
the
case
unprotected
unstrained
N‐heterocycles,
reactions
offer
ammonium
selenonitriles
that
prove
to
be
an
efficient
selenonitrile
reagent.
magnified
image
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(19), P. 13350 - 13359
Published: Sept. 13, 2021
A
practical
and
scalable
ortho-selective
deuteration
of
aromatic
aldehydes
was
accomplished
by
Pd-catalyzed
hydrogen
isotope
exchange
with
deuterium
oxide
as
an
inexpensive
source.
The
use
tert-leucine
a
transient
directing
group
facilitates
the
exchange,
affording
wide
range
ortho-deuterated
incorporation
up
to
97%.
control
experiments
suggest
that
addition
silver
trifluoroacetate
resists
unexpected
reduction
Pd(II),
while
theoretical
study
indicates
rapid
reversible
concerted
metalation–deprotonation
process.
