Nickel-Catalyzed Inter- and Intramolecular Reductive Cross-Coupling Reactions of Arylbenzylammonium Salts through Highly Site-Selective C–N Bond Cleavage
ACS Catalysis,
Год журнала:
2024,
Номер
14(7), С. 5039 - 5046
Опубликована: Март 20, 2024
The
site
selectivity
has
been
investigated
for
the
C–N
bond
cleavage
of
arylbenzylammonium
salts
in
reductive
cross-coupling
reactions
with
carbon
electrophiles.
A
wide
variety
triflates
participated
nickel-catalyzed
zinc-mediated
benzyl–aryl
cross-electrophile
coupling
aryl
bromides
to
afford
diarylmethanes
extremely
high
selectivity.
same
reaction
conditions
were
successfully
extended
intramolecular
benzyl(bromoaryl)ammonium
triflates.
Moreover,
underwent
manganese-mediated
benzyl–acyl
aromatic
carboxylic
acids
presence
di-tert-butyl
pyrocarbonate.
These
employ
readily
available
feedstocks
and
reagents,
exhibit
benzylic
bonds
rather
than
bonds,
tolerate
a
functional
groups.
Язык: Английский
Strategies for Using Quaternary Ammonium Salts as Alternative Reagents in Alkylations
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(33)
Опубликована: Апрель 8, 2024
Alkylation
reactions
are
pivotal
in
organic
chemistry,
with
wide-ranging
utilization
across
various
fields
of
applied
synthetic
chemistry.
However,
conventional
reagents
employed
alkylations
often
pose
substantial
health
and
exposure
risks.
Quaternary
ammonium
salts
(QAS)
present
a
promising
alternative
for
these
transformations
offering
significantly
reduced
hazards
as
they
non-cancerogenic,
non-mutagenic,
non-flammable,
non-corrosive.
Despite
their
potential,
use
direct
remains
relatively
unexplored.
This
review
outlines
strategies
utilizing
QAS
alkylation
reactions,
providing
researchers
safer
approaches
to
chemical
synthesis.
Язык: Английский
Access to 2-Alkyltropones via Organic Base-Catalyzed Tandem Deamination and Aldol Condensation of Tropinone-Derived Quaternary Ammonium Salts
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(23), С. 16456 - 16466
Опубликована: Ноя. 10, 2023
The
tropone
skeleton
exists
in
a
number
of
natural
products
and
bioactive
substances,
currently,
the
applications
substituted
tropones
are
significantly
limited
by
their
preparative
methods.
Herein,
we
report
very
convenient
method
to
access
2-alkyltropones
via
organic
base-catalyzed
tandem
reaction
tropinone-derived
quaternary
ammonium
salts.
Tropinone
methiodide
reacted
with
wide
variety
aromatic
aliphatic
aldehydes
presence
1,4-diazabicyclo[2.2.2]octane
afford
structurally
diverse
moderate
excellent
yields
extremely
high
site
selectivity.
employs
readily
available
feedstocks
reagents,
is
free
transition
metals
compatible
water
air,
tolerates
functional
groups,
can
be
easily
scaled
up.
Moreover,
amenable
various
synthetic
transformations.
Preliminary
mechanistic
studies
revealed
that
proceeded
deamination,
aldol
condensation,
isomerization.
Язык: Английский