Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(69)
Опубликована: Сен. 8, 2023
Homoleptic
[L-I-L]+
iodine(I)
complexes
(where
L
is
a
R3
R2
R1
N
tertiary
amine)
were
synthesized
via
the
[L-Ag-L]+
→
cation
exchange
reaction.
In
solution,
amines
form
[R3
N-Ag-NR1
]+
silver(I)
complexes,
which
crystallize
out
from
solution
as
meso-[L-Ag-L]+
characterized
by
X-ray
crystallography.
The
subsequent
analogues
extremely
reactive
and
could
not
be
isolated
in
solid
state.
Density
functional
theory
(DFT)
calculations
performed
to
study
Ag+
-N
I+
interaction
energies
with
former
ranging
-80
-100
kJ
mol-1
latter
-260
-279
.
crystal
structures
revealed
⋅⋅⋅Cπ
⋅⋅⋅H-C
short
contacts
between
flexible
N-alkyl/N-aryl
groups,
are
first
of
their
kind
such
precursor
complexes.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(21), С. 4393 - 4397
Опубликована: Янв. 1, 2023
Herein,
we
describe
a
B(C
6
F
5
)
3
-catalyzed
redox-neutral
β-functionalization
of
tertiary
amines
with
cyclic-ketimines,
achieving
various
1,3-diamines
containing
the
indolin-3-one
moiety
via
borrowing
hydrogen
strategy.
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
61(35)
Опубликована: Июль 4, 2022
Abstract
We
designed
a
borane/gold(I)
co‐catalytic
system
and
used
it
for
C−H
functionalization
reactions
cycloaddition
between
tertiary
amines
α‐alkynylenones.
Both
effectively
incorporated
furan
ring
into
the
amine.
Chemical Science,
Год журнала:
2021,
Номер
13(3), С. 775 - 780
Опубликована: Дек. 20, 2021
An
unprecedented
redox-neutral
annulation
reaction
of
tertiary
anilines
with
electron-deficient
alkynes
was
developed
that
proceeds
through
a
cascade
Friedel-Crafts
alkylation/[1,5]-hydride
transfer/Mannich
cyclization
sequence.
Under
B(C6F5)3
catalysis,
range
functionalized
1,2,3,4-tetrahydroquinolines
were
facilely
constructed
in
moderate
to
good
yields
exclusive
3,4-anti-stereochemistry.
The
commercial
availability
the
catalyst
and
high
atom
step
economy
procedure,
together
metal-free
external
oxidant-free
conditions,
make
this
an
attractive
method
organic
synthesis.
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
61(50)
Опубликована: Окт. 10, 2022
Silanes
are
important
in
chemistry
and
material
science.
The
self-redistribution
of
HSiCl3
is
an
industrial
process
to
prepare
SiH4
,
which
widely
used
electronics
automobile
industries.
However,
selective
silane
cross-redistribution
advanced
silanes
challenging.
We
now
report
enthalpy-driven
access
bis-silanes
that
contain
two
different
types
Si-H
bonds
the
same
molecule.
Compared
with
entropy-driven
reactions,
reaction
shows
high
regioselectivity,
broad
substrate
scope
(62
examples)
atom
economy.
Our
combined
experimental
computational
study
indicates
proceeds
through
a
Ni0
-NiII
-NiIV
catalytic
cycle.
ACS Catalysis,
Год журнала:
2024,
Номер
14(10), С. 8041 - 8049
Опубликована: Май 8, 2024
The
reason
for
the
site
selectivity
previously
reported
B(C6F5)3-catalyzed
C(sp3)–H
alkylation
of
tertiary
amines
with
electron-deficient
olefins
remains
a
mystery.
appears
to
be
governed
by
number
electron-withdrawing
groups
(EWGs)
on
olefin:
one
EWG
results
in
α-alkylation,
whereas
two
EWGs
(one
each
end
double
bond)
result
β-alkylation.
In
this
study,
we
solved
mystery
and
unlocked
pathway
β-alkylation
bearing
only
EWG.
Control
experiments
density
functional
theory
calculations
provided
detailed
picture
reaction
mechanism
both
α-
Furthermore,
demonstrated
broad
scope
reaction.
Nature Communications,
Год журнала:
2023,
Номер
14(1)
Опубликована: Фев. 9, 2023
Abstract
Sila-isosteres
have
attracted
increasing
attention
due
to
their
potential
application
in
a
variety
of
fields
and
different
properties
compared
carbon-containing
analogs.
However,
the
preparation
these
silicon-containing
compound
remains
challenging
thus
development
alternative
synthetic
methodologies
is
desirable.
Here,
we
employ
B(C
6
F
5
)
3
as
catalyst
enable
synthesis
highly
functionalized
sila-benzoazoles
via
hydrosilylation
rearrangement
cascade
reaction
benzoazoles
commercially
available
silanes.
This
strategy
also
exhibits
remarkable
features
such
100%
atom-economy,
good
functional
group
tolerance,
broad
substrate
scope,
easy
scale-up
catalytic
performance,
demonstrating
its
sila-isostere
synthesis.
Organic Letters,
Год журнала:
2022,
Номер
25(1), С. 109 - 114
Опубликована: Дек. 9, 2022
With
triethylamine
as
a
vinylene
source,
convenient
protocol
for
the
regioselective
synthesis
of
β,γ-nonsubstituted
2-arylquinolines
from
aldehydes
and
arylamines
has
been
accomplished.
The
deaminative
cyclization
is
also
extended
to
long-chain
tertiary
alkylamines,
enabling
diverse
alkyl
groups
be
concurrently
installed
into
pyridine
rings.
This
process
demonstrates
new
conversion
pathway
simultaneous
dual
C(sp3)-H
bond
functionalization
amines,
wherein
transient
acyclic
enamines
generated
in
situ
undergo
Povarov
reaction.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(6), С. 4244 - 4248
Опубликована: Фев. 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).
Chemical Science,
Год журнала:
2023,
Номер
14(15), С. 4114 - 4119
Опубликована: Янв. 1, 2023
A
palladium-catalyzed
synthesis
of
4-sila-4
H
-benzo[
d
][1,3]oxazines,
silicon-switched
analogs
biologically
relevant
4
was
developed
by
the
intramolecular
Hiyama
coupling
3-amido-2-(arylsilyl)aryl
triflates.
