European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(35)
Published: July 27, 2023
Abstract
A
Friedel–Crafts
reaction
of
indolizines
with
2‐aryl‐3
H
‐indol‐3‐ones
catalyzed
by
B(C
6
F
5
)
3
is
described.
This
protocol
gives
access
to
indolizine
derivatives
that
are
valuable
building
blocks
in
synthetic
and
pharmaceutical
chemistry.
The
proceeds
under
mild
conditions,
affording
various
C2‐quaternary
indolin‐3‐ones
based
on
high
yields
regioselectivities.
Moreover,
the
transformations
target
products
were
realized
N‐methylation
trifluoromethane
sulfonation.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(7), P. 4856 - 4864
Published: March 18, 2024
Pyrroles
are
important
N-heterocycles
found
in
medicines
and
materials.
The
formation
of
pyrroles
from
widely
accessible
pyrrolidines
is
a
potentially
attractive
strategy
but
an
underdeveloped
approach
due
to
the
sensitivity
oxidative
conditions
required
achieve
such
transformation.
Herein,
we
report
catalytic
that
employs
commercially
available
B(C6F5)3
operationally
simple
procedure
allows
serve
as
direct
synthons
for
pyrroles.
Mechanistic
studies
have
revealed
insights
into
borane-catalyzed
dehydrogenative
processes.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(27)
Published: March 29, 2024
Abstract
Inverse
hydride
shuttle
catalysis
provides
a
multicomponent
platform
for
the
highly
efficient
synthesis
of
alkaloid
frameworks
with
exquisite
diastereoselectivity.
However,
number
limitations
hinder
this
method,
primarily
strict
requirement
electron‐deficient
acceptors.
Herein,
we
present
general
Lewis
acid‐driven
approach
to
address
constraint,
and
have
developed
two
broad
strategies
enabling
modular
complex
azabicycles
that
were
entirely
unattainable
using
previous
method.
The
enhanced
synthetic
flexibility
facilitates
streamlined
asymmetric
cyclization,
leading
concise
total
(−)‐tashiromine.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(6), P. 4244 - 4248
Published: Feb. 23, 2024
Herein,
we
report
a
synthetic
method
to
access
range
of
highly
substituted
indoles
via
the
B(C6F5)3-catalyzed
transfer
2°
alkyl
groups
from
amines.
The
transition-metal-free
catalytic
approach
has
been
demonstrated
across
broad
and
amine
donors,
including
various
substituents
on
both
reacting
components,
useful
C(3)-alkylated
indole
products.
process
can
be
performed
using
Schlenk
line
techniques
in
combination
with
commercially
available
B(C6F5)3·nH2O
solvents,
which
obviates
requirement
for
specialized
equipment
(e.g.,
glovebox).
Synlett,
Journal Year:
2023,
Volume and Issue:
34(18), P. 2117 - 2128
Published: June 16, 2023
Abstract
C–H
functionalization
is
widely
regarded
as
an
important
area
in
the
development
of
synthetic
methodology,
enabling
design
more
time-
and
atom-efficient
syntheses.
The
ability
electron-deficient
organoboranes
to
mediate
hydride
abstraction
from
α-amino
bonds
therefore
great
interest,
reactive
iminium
hydridoborate
moieties
generated
are
able
participate
a
range
synthetically
useful
transformations.
In
this
review,
we
cover
recent
advances
made
organoborane-mediated
abstraction,
focus
on
catalytic
applications
boranes
α-
or
β-functionalization,
α,β-difunctionalization,
dehydrogenation
amines.
1
Introduction
2
α-Functionalization
Amines
3
β-Functionalization
4
α,β-Difunctionalization
5
Dehydrogenation
6
Summary
Future
Prospects
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(34), P. 6903 - 6913
Published: Jan. 1, 2023
A
one-pot
synthesis
of
1,2,5-trisubstituted-1,2-dihydro-3
H
-pyrrole-3-thiones
(up
to
91%
yield)
by
the
successive
treatment
available
propargylamines
with
acyl
chlorides
(PdCl
2
/CuI/Ph
3
P/Et
N,
toluene,
40–45
°C,
h)
and
sodium
sulfide
(Na
S·9H
O,
EtOH,
20–25
7
has
been
developed.
Chemistry - An Asian Journal,
Journal Year:
2023,
Volume and Issue:
18(18)
Published: Aug. 2, 2023
Abstract
A
facile
enantioselective
alkynylation
of
cyclic
ketimines
attached
to
a
neutral
functional
group
utilizing
the
dual
Cu(I)‐CPA
catalysis
is
described.
The
strategy
2‐aryl‐3
H
‐indol‐3‐one
directly
chiral
propargylic
amines
containing
indolin‐3‐one
moiety
in
good
yields
and
enantioselectivities.
Moreover,
gram‐scale
synthesis
propargylamines
based
C2‐quaternary
indolin‐3‐ones
was
performed.
synthetic
applications
were
confirmed
by
transformations
products
with
no
decrease
yield
enantioselectivity.
Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
136(5)
Published: Dec. 14, 2023
Abstract
Functionalization
of
the
C(sp
3
)−H
bonds
trialkylamines
is
challenging,
especially
for
reactions
at
positions
other
than
α
position.
Herein,
we
report
a
method
β‐C(sp
allylation
trialkylamines.
In
these
reactions,
which
involve
synergistic
borane/palladium
catalysis,
an
enamine
intermediate
first
generated
from
amine
via
α,β‐dehydrogenation
promoted
by
B(C
6
F
5
)
and
base,
then
undergoes
palladium‐catalyzed
reaction
with
allene
to
give
product.
Because
hydride
proton
resulting
initial
dehydrogenation
are
ultimately
shuttled
product
palladium
catalyst,
respectively,
show
excellent
atom
economy.
The
establishment
this
paves
way
future
studies
C−H
functionalization
means
borane/transition‐metal
catalysis.
Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
136(27)
Published: March 29, 2024
Abstract
Inverse
Hydrid‐Shuttle
Katalyse
bildet
eine
Plattform
für
die
hocheffiziente
und
diastereoselektive
Synthese
von
Alkaloidstrukturen
durch
Multikomponentenreaktionen.
Mehrere
Einschränkungen
hindern
jedoch
breite
Anwendbarkeit
dieses
Ansatzes,
darunter
vor
allem
Notwendigkeit
nach
besonders
elektronenarmen
Akzeptoren.
Hier
präsentieren
wir
einen
allgemeinen,
Lewis
Säuren
getriebenen
Ansatz,
um
diese
Einschränkung
anzugehen,
haben
zwei
Strategien
entwickelt,
modulare
komplexer
azabicyclischer
Systeme
ermöglichen,
mit
der
früheren
Methode
unerreichbar
waren.
Die
so
gewonnene
synthetische
Flexibilität
führt
zu
einer
verbesserten
asymmetrischen
Cyclisierung,
kurze
Totalsynthese
des
Alkaloids
(−)‐Tashiromin
ermöglicht
hat.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(31)
Published: June 7, 2024
Abstract
Here,
we
have
successfully
achieved
the
addition
of
difluoroacetate
radicals
to
2‐aryl‐3
H
‐indol‐3‐ones,
enabling
various
difluoroalkylations
C2‐tetrasubstituted
2‐aryl
indolin‐3‐ones
in
a
highly
efficient
and
economical
manner.
It
is
worth
mentioning
that
these
difluoroalkylation
compounds
can
be
easily
transformed
into
derivatives
under
mild
reaction
conditions.
Control
experiments
suggest
involvement
ethyl
radical
species
reaction.
