Frontiers in Chemistry,
Год журнала:
2022,
Номер
10
Опубликована: Сен. 13, 2022
A
metal-free
catalytic
approach
for
the
remote
C6-functionalization
of
2,3-disubstituted
indoles
has
been
developed.
In
presence
amounts
Brønsted
acid,
β,γ-unsaturated
α-ketoesters
react
with
at
C6
position
selectively.
Under
mild
reaction
conditions,
a
range
C6-functionalized
were
prepared
good
yields
and
excellent
regioselectivity.
This
methodology
provides
concise
efficient
route
synthesis
indole
derivatives.
Organic Letters,
Год журнала:
2023,
Номер
25(10), С. 1711 - 1716
Опубликована: Март 9, 2023
Herein,
we
described
a
highly
regio-
and
enantioselective
Friedel–Crafts
alkylation
of
aniline
derivatives
with
in
situ
generated
ortho-quinone
methides
enabled
by
chiral
phosphoric
acid,
furnishing
wide
range
enantioenriched
triarylmethanes
bearing
three
similar
benzene
rings
high
yields
(up
to
98%)
excellent
stereoselectivities
98%
ee).
Furthermore,
the
large-scale
reactions
diversified
transformations
product
demonstrate
practicality
protocol.
Density
functional
theory
calculations
elucidate
origin
enantioselectivity.
Abstract
Herein,
the
first
diversity‐oriented
catalytic
asymmetric
dearomatization
of
indoles
with
o
‐quinone
diimides
(
‐QDIs)
is
reported.
The
(CADA)
one
research
focuses
in
terms
structural
and
biological
importance
dearomatized
indole
derivatives.
Although
great
achievements
have
been
made
target‐oriented
CADA
reactions,
reactions
are
regarded
as
more
challenging
remain
elusive
due
to
lack
synthons
featuring
multiple
reaction
sites
difficulty
precise
control
chemo‐,
regio‐,
enantio‐selectivity.
In
this
work,
‐QDIs
employed
a
versatile
building
block,
enabling
chemo‐divergent
dearomative
arylation
[4
+
2]
cycloaddition
indoles.
Under
catalysis
chiral
phosphoric
acid
mild
conditions,
various
indolenines,
furoindolines/pyrroloindolines,
six‐membered‐ring
fused
indolines
collectively
prepared
good
yields
excellent
enantioselectivities.
This
synthesis
protocol
enriches
chemistry
offers
new
opportunities
for
reactions.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(15)
Опубликована: Фев. 8, 2023
Abstract
Nitrogen‐containing
heterocyclic
compounds
have
consistently
been
a
noticeable
center
of
attention
due
to
their
significant
utilization
in
the
domain
synthetic
organic
chemistry,
agrochemicals,
and
pharmaceuticals.
α,β‐Unsaturated
imines
or
conjugated
provide
lot
cyclic
as
well
acyclic
products
through
reacting
with
versatile
family
compounds.
This
review
summarizes
recent
advances
enantioselective
reactions
α,β‐unsaturated
by
using
methodologies
for
synthesizing
various
nitrogen‐containing
heterocycles
that
contain
four
six‐membered
rings.
The
synthesis
rarely
found
seven‐,
eight‐
nine‐membered
also
reported.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(16)
Опубликована: Март 13, 2023
Abstract
Copper‐catalyzed
1,4‐addition
of
a
silicon
nucleophile
to
azadienes
is
reported.
This
method
facilely
provided
wide
variety
dibenzylic
silane
derivatives
in
good
excellent
yields.
The
important
practical
features
are
the
use
cheap
catalytic
system,
mild
reaction
conditions,
and
broad
substrate
scope.
Organic Letters,
Год журнала:
2022,
Номер
24(8), С. 1727 - 1731
Опубликована: Фев. 24, 2022
Compared
with
the
well-established
asymmetric
Pictet-Spengler
reactions
on
pyrrole
ring
of
indoles,
catalytic
reaction
benzene
indoles
has
been
rarely
studied.
Herein
C6-selective
have
realized
by
employing
2-(1H-indol-7-yl)anilines
and
isatins
in
presence
chiral
phosphoric
acid,
affording
novel
polycyclic
indole
derivatives
bearing
spiro
quaternary
stereocenters
excellent
yields
enantioselectivities.
This
could
be
conducted
gram
scale
without
any
loss
activity
or
enantioselectivity.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
366(4), С. 774 - 779
Опубликована: Окт. 26, 2023
Abstract
Rh‐catalyzed
asymmetric
C(
sp
3
)−H
arylation
of
8‐benzylquinolines
with
arylboronic
acids
was
developed.
In
the
presence
5
mol%
BINOL‐derived
chiral
cyclopentadienyl
rhodium
complex,
benzylic
bond
reaction
proceeded
smoothly
to
afford
a
series
enantioenriched
triarylmethanes
in
moderate
good
yields
excellent
enantioselective
control
(24–89%
yields,
63–93%
ee).
The
method
displays
broad
substrate
scope
and
functional
group
tolerance
under
mild
conditions.
Royal Society of Chemistry eBooks,
Год журнала:
2024,
Номер
unknown, С. 109 - 231
Опубликована: Фев. 21, 2024
This
chapter
shows,
as
in
previous
years,
the
most
important
achievements
of
2021
year
area
organo-phosphorus
compounds
containing:
three
P–O
bonds
(Section
2:
phosphoric
acids
and
their
derivatives),
two
one
P–C
3:
phosphonic
derivatives)
well
4:
phosphinic
addition
to
phosphoryl
group
P═O,
present
all
groups
compounds.
Each
main
sections
covers
“synthesis
reactions”
including
pure
synthesis
without
applications,
biological
applications”
miscellaneous
directed
towards
non-biological
applications.
At
end
each
subsection,
corresponding
are
shown
for
hetero-analogues
which
phosphorus–oxygen
have
been
replaced
by
phosphorus–heteroatom
P–X
and/or
P═Y
(X,
Y
=
N,
S
or
Se).
The
subsection
on
quinquevalent
phosphorus
derivatives
catalysts
has
placed,
usual,
at
entire
chapter,
after
a
review
As
devoted
dominated
over
smaller
section
derivatives,
literature
references
these
remained
ratio
4
:
12
1.
A
dynamic,
five-fold
increase
number
works,
subject
chiral
catalysts,
recorded
this
year.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(5), С. 3132 - 3147
Опубликована: Фев. 13, 2023
Indium-catalyzed,
solvent-enabled
regioselective
C6-
or
N1-alkylations
of
2,3-disubstituted
indoles
with
para-quinone
methides
are
developed
under
mild
conditions.
Notably,
highly
selective
and
switchable
alkylations
were
selectively
achieved
by
adjusting
the
reaction
Moreover,
scalability
further
transformations
alkylation
products
demonstrated,
this
operationally
simple
methodology
is
amenable
to
late-stage
C6-functionalization
indomethacin
drug.
The
pathways
explained
support
experimental
density
functional
theory
studies.
