The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(21), С. 14840 - 14845
Опубликована: Окт. 21, 2022
Herein,
we
disclose
a
strategy
to
realize
α,β-difunctionalization
and
C–N
bond
cleavage
of
saturated
amines
with
benzo[c]isoxazoles
via
B(C6F5)3-catalyzed
consecutive
hydrogen-borrowing
[4
+
2]
cycloaddition
followed
by
process.
In
general,
the
reactions
proceed
efficiently
in
absence
any
oxidant
metal
catalyst
afford
broad
range
quinoline
derivatives
starting
from
easily
accessible
substrates
an
atom-economical
manner.
Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
8(16), С. 4582 - 4606
Опубликована: Янв. 1, 2021
Functionalized
cyclic
amines
are
the
essential
structural
moieties
of
numerous
biologically
active
compounds.
This
review
summarized
most
recent
advances
in
C–H,
C–N
and
C–C
bond
functionalization
saturated
amines.
ACS Catalysis,
Год журнала:
2024,
Номер
14(7), С. 4856 - 4864
Опубликована: Март 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.
Journal of the American Chemical Society,
Год журнала:
2021,
Номер
143(5), С. 2441 - 2455
Опубликована: Янв. 29, 2021
We
disclose
a
catalytic
method
for
β-C(sp3)–H
functionalization
of
N-alkylamines
the
synthesis
enantiomerically
enriched
β-substituted
amines,
entities
prevalent
in
pharmaceutical
compounds
and
used
to
generate
different
families
chiral
catalysts.
demonstrate
that
catalyst
system
comprising
seemingly
competitive
Lewis
acids,
B(C6F5)3,
Mg-
or
Sc-based
complex,
promotes
highly
enantioselective
union
α,β-unsaturated
compounds.
An
array
δ-amino
carbonyl
was
synthesized
under
redox-neutral
conditions
by
reaction
N-alkylamine-derived
enamine
an
electrophile
activated
acid
co-catalyst.
The
utility
approach
is
highlighted
late-stage
β-C–H
bioactive
amines.
Investigations
regard
mechanistic
nuances
processes
are
described.
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.
Organic Letters,
Год журнала:
2023,
Номер
25(15), С. 2722 - 2727
Опубликована: Апрель 12, 2023
A
one-pot
umpolung
method
for
the
ring-opening
pyridylation
of
unstrained
cyclic
amines
was
developed
using
N-amidopyridinium
salts.
This
process
involves
formation
electron
donor-acceptor
complexes
between
bromide
and
salts,
ultimately
leading
to
functionalization
pyridines.
protocol
is
compatible
with
a
range
5-
or
6-membered
pyridines,
thereby
providing
powerful
synthon
preparing
C4-functionalized
pyridines
under
visible-light
conditions
in
absence
an
external
photocatalyst.
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.
