Synlett,
Год журнала:
2018,
Номер
29(07), С. 845 - 855
Опубликована: Фев. 19, 2018
The
dearomatization
of
arenes
is
a
fundamental
synthetic
strategy,
providing
direct
connection
between
simple
hydrocarbons
and
valuable,
more
complex
intermediates.
While
several
strategies
exist,
the
functionalization
with
concurrent
introduction
functionality
(i.e.,
dearomative
functionalization)
still
largely
underdeveloped
field.
This
Synpacts
article
provides
an
overview
insights
from
our
recent
work
in
this
area
using
small
molecules—arenophiles.
1
Introduction
2
Arenophiles
3
Olefin-Like
Dearomative
Functionalizations
4
Transition-Metal
Catalysis
5
Applications
Natural
Product
Synthesis
6
Conclusion
Angewandte Chemie,
Год журнала:
2019,
Номер
131(31), С. 10570 - 10586
Опубликована: Янв. 31, 2019
Abstract
Die
Arenhydrierung
bietet
einen
direkten
Zugang
zu
gesättigten
Carbo‐
und
Heterocyclen
kann
daher
zur
Verkürzung
von
Synthesewegen
genutzt
werden.
Diese
nützliche
Transformation
wird
industriell
verwendet
sollte
weitere
Durchbrüche
in
den
angewandten
Wissenschaften
ermöglichen.
Von
zentraler
Bedeutung
für
die
Anwendung
bei
der
Herstellung
komplexer
Moleküle
ist
Kontrolle
Diastereo‐,
Enantio‐
Chemoselektivität.
Im
Allgemeinen
ergibt
Hydrierung
multisubstituierter
Arene
überwiegend
das
cis‐Isomer.
Enantiokontrolle
über
chirale
Auxiliare,
Brønsted‐Säuren
oder
Übergangsmetallkatalysatoren
erfolgen.
Jüngere
Arbeiten
zeigen
hoch
chemoselektive
Transformationen.
Derartige
Verfahren
zugrunde
liegenden
Strategien
werden
hier
erläutert,
wobei
Schwerpunkt
auf
präparativ
nützlichen
Reaktion
mit
leicht
verfügbaren
Katalysatoren
liegt.
ACS Catalysis,
Год журнала:
2019,
Номер
9(9), С. 8555 - 8560
Опубликована: Авг. 16, 2019
As
significant
pharmacophores,
1,3-disubstituted
cyclohexanes
are
widespread
in
natural
products
and
synthetic
bioactive
molecules.
In
this
work,
we
describe
a
palladium-catalyzed
arylboration
of
1,4-cyclohexadienes,
which
allows
expeditious
access
to
an
array
functionalized
from
the
readily
available
starting
materials.
Palladium
catalysis
enables
proceed
reversed
regioselectivity
compared
with
earlier
nickel
catalysis.
The
most
striking
feature
protocol
lies
1,3-regioselectivity
exclusive
cis-diastereoselectivity.
Intriguingly,
success
three-component
reaction
does
not
rely
on
application
dative
ligands
but
cheap
ammonium
chloride
salt
instead.
utility
method
is
highlighted
by
series
downstream
stereospecific
transformations
drug
molecule
synthesis.
Journal of the American Chemical Society,
Год журнала:
2022,
Номер
145(1), С. 25 - 31
Опубликована: Дек. 22, 2022
Heterocycles
are
the
backbone
of
modern
medical
chemistry
and
drug
development.
The
derivatization
"an
olefin"
inside
aromatic
rings
represents
an
ideal
approach
to
access
functionalized
saturated
heterocycles
from
abundant
building
blocks.
Here,
we
report
operationally
simple,
efficient,
practical
method
selectively
hydrosilylated
reduced
N-heterocycles
bicyclic
aromatics
via
a
key
diradical
intermediate.
This
is
expected
facilitate
complex
heterocycle
functionalizations
that
enable
novel
medicinally
relevant
scaffolds.
Chemical Communications,
Год журнала:
2017,
Номер
53(75), С. 10390 - 10393
Опубликована: Янв. 1, 2017
The
cyclohexa-1,3-diene
motif
is
introduced
as
an
equally
effective
alternative
to
the
cyclohexa-1,4-diene
platform
in
B(C6F5)3-catalysed
transfer
processes.
hydrogenation
of
alkenes
realised
with
α-terpinene
and
related
hydrosilylation
achieved
5-trimethylsilyl-substituted
cyclohexa-1,3-diene.
Both
yields
substrate
scope
are
comparable
prior
systems.
Synlett,
Год журнала:
2018,
Номер
29(07), С. 845 - 855
Опубликована: Фев. 19, 2018
The
dearomatization
of
arenes
is
a
fundamental
synthetic
strategy,
providing
direct
connection
between
simple
hydrocarbons
and
valuable,
more
complex
intermediates.
While
several
strategies
exist,
the
functionalization
with
concurrent
introduction
functionality
(i.e.,
dearomative
functionalization)
still
largely
underdeveloped
field.
This
Synpacts
article
provides
an
overview
insights
from
our
recent
work
in
this
area
using
small
molecules—arenophiles.
1
Introduction
2
Arenophiles
3
Olefin-Like
Dearomative
Functionalizations
4
Transition-Metal
Catalysis
5
Applications
Natural
Product
Synthesis
6
Conclusion
