Molecules,
Год журнала:
2022,
Номер
27(16), С. 5201 - 5201
Опубликована: Авг. 15, 2022
Among
the
variety
of
sulfonamides,
triflamides
(CF3SO2NHR,
TfNHR)
occupy
a
special
position
in
organic
chemistry.
Triflamides
are
widely
used
as
reagents,
efficient
catalysts
or
additives
numerous
reactions.
The
reasons
for
widespread
use
these
compounds
their
high
NH-acidity,
lipophilicity,
catalytic
activity
and
specific
chemical
properties.
Their
strong
electron-withdrawing
properties
low
nucleophilicity,
combined
with
makes
it
possible
to
vast
This
review
is
devoted
synthesis
N-trifluoromethanesulfonyl
derivatives
chemistry,
medicine,
biochemistry,
catalysis
agriculture.
Part
work
areas
examples
bis(trifluoromethanesulfonyl)imide
(triflimide,
(CF3SO2)2NH,
Tf2NH).
Being
one
strongest
NH-acids,
triflimide,
especially
its
salts,
cycloaddition
reactions,
Friedel–Crafts
condensation
heterocyclization
many
others.
act
source
nitrogen
C-amination
(sulfonamidation)
products
which
useful
building
blocks
synthesis,
ligands
metal
complex
catalysis,
have
found
applications
medicine.
addition
reactions
triflamide
presence
oxidizing
agents
alkenes
dienes
considered
separately.
Chemical Reviews,
Год журнала:
2020,
Номер
121(14), С. 8756 - 8867
Опубликована: Ноя. 23, 2020
This
review
describes
the
gold-catalyzed
reactions
of
specially
activated
alkynes,
allenes,
and
alkenes.
Such
species
are
characterized
by
presence
either
electron-donating
or
electron-withdrawing
groups
as
substituents
carbon
π-system.
They
intrinsically
polarized,
when
compared
to
their
nonspecially
counterparts
can
therefore
be
involved
in
transformations
featuring
increased
regio-,
stereo-,
chemoselectivities.
The
chemistry
π-systems
under
homogeneous
gold
catalysis
is
extremely
rich
varied.
reactivity
observed
with
unsaturated
systems
often
transposed
ones
without
loss
efficiency.
However,
also
exhibit
specific
reactivities
that
cannot
attained
regular
substrates.
In
this
family
π-systems,
ynamides
analogs,
along
alkynyl
carbonyl
derivatives,
classes
substrates
have
retained
most
attention.
provides
an
overview
developed
all
discussing
general
reactivities,
presenting
commenting
on
well
applications.
Chemical Reviews,
Год журнала:
2021,
Номер
121(14), С. 8478 - 8558
Опубликована: Фев. 8, 2021
The
catalyst-directed
divergent
synthesis,
commonly
termed
as
"divergent
catalysis",
has
emerged
a
promising
technique
it
allows
chartering
of
structurally
distinct
products
from
common
substrates
simply
by
modulating
the
catalyst
system.
In
this
regard,
gold
complexes
powerful
catalysts
they
offer
unique
reactivity
profiles
compared
to
various
other
transition
metal
catalysts,
primarily
due
their
salient
electronic
and
geometrical
features.
Owing
tunable
soft
π-acidic
nature,
not
only
evolved
superior
contenders
for
catalyzing
reactions
alkynes,
alkenes,
allenes
but
also,
more
intriguingly,
have
been
found
provide
reaction
pathways
over
π-acid
such
Ag,
Pt,
Pd,
Rh,
Cu,
In,
Sc,
Hg,
Zn,
etc.
recent
past
witnessed
renaissance
in
examples
wherein,
choosing
or
fine-tuning
ligands,
counteranions
oxidation
states
itself,
complete
switch
was
observed.
However,
reviews
documenting
are
sporadic;
result,
most
reports
kind
remained
scattered
literature,
thereby
hampering
further
development
burgeoning
field.
By
conceptualizing
idea
"Divergent
Gold
Catalysis
(DGC)",
review
aims
consolidate
all
unified
approach
necessary
pave
way
advancement
exciting
area.
Based
on
factors
governing
divergence
product
formation,
an
explicit
classification
DGC
provided.
To
gain
fundamental
understanding
observed
reactivities
selectivities,
is
accompanied
mechanistic
insights
at
appropriate
places.
Frontiers in Chemistry,
Год журнала:
2019,
Номер
7
Опубликована: Май 14, 2019
Gold
is
currently
one
of
the
most
used
metals
in
organometallic
catalysis.
The
ability
gold
to
activate
unsaturated
groups
different
modes,
together
with
its
tolerance
a
wide
range
functional
and
reaction
conditions,
turns
gold-based
complexes
into
efficient
highly
sought
after
catalysts.
Natural
products
relevant
compounds
biological
pharmaceutical
activity
are
often
characterized
by
complex
molecular
structures.
(Cyclo)isomerization
reactions
useful
strategy
for
generation
this
complexity
from
synthetically
accesible
reactants.
In
review,
we
collect
recent
contributions
which
gold(I)-
and/or
gold(III)-catalysts
mediate
intramolecular
(cyclo)isomerization
transformations
species,
commonly
feature
allene
or
alkyne
motifs,
organize
them
depending
on
substrate
type.
Organic Letters,
Год журнала:
2019,
Номер
21(12), С. 4469 - 4474
Опубликована: Июнь 5, 2019
A
modular
and
streamlined
synthetic
strategy
for
the
generation
of
bridged
indole
alkaloid-like
heterocycles
from
easily
available
building
blocks
is
elaborated.
This
approach
utilizes
an
Ugi
four-component
reaction,
establishing
diversity,
followed
by
efficient
cationic
gold-triggered
intramolecular
cascade
non-oxidative
dearomative
spirocarbocyclization/concerted
[4
+
2]
cyclization
cascade,
furnishing
these
architecturally
complex
distinct
heterocyclic
scaffolds
with
good
diastereoselectivity.
Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
8(13), С. 3543 - 3593
Опубликована: Янв. 1, 2021
This
review
gives
an
insight
into
the
most
recent
synthetic
methodologies
towards
spiro-γ-lactams,
a
class
of
compounds
that
are
present
in
wide
range
bioactive
and
naturally
occurring
molecules.
The Journal of Organic Chemistry,
Год журнала:
2019,
Номер
85(4), С. 1906 - 1914
Опубликована: Дек. 10, 2019
A
facile
protocol
for
the
tunable
synthesis
of
10-hydroxy-1-azaspiro[4.5]deca-3,6,8-trien-2-ones
and
benzo[b]pyrrolo[2,1-c][1,4]oxazin-3-ones
is
described.
has
been
realized
by
use
ZnBr2/oxone
tetra-n-butylammonium
bromide
(TBAB)/oxone.
The
reaction
proceeds
smoothly
with
high
efficiency
a
broad
substrate
scope.
Mechanistic
studies
indicate
that
an
N-protecting
group-assisted
ortho-trapping
involved.
In
transformation,
undergoes
α-addition,
ipso-cyclization,
resulting
spirocyclic
species.
The Journal of Organic Chemistry,
Год журнала:
2020,
Номер
85(23), С. 15092 - 15103
Опубликована: Ноя. 17, 2020
The
development
of
a
rapid
and
diverse
access
to
complex
natural
product-like
3,4-fused
indole
scaffolds
has
always
attracted
considerable
attention
from
synthetic
medicinal
communities.
We
herein
disclose
modular
straightforward
protocol
prepare
the
densely
substituted
polycyclic
azepino[5,4,3-cd]indole
scaffolds.
This
process
involves
an
Ugi
four-component
reaction
easily
available
starting
materials
gold-catalyzed
post-Ugi
domino
dearomatization/Michael
addition
sequence,
enabling
facile
highly
functionalized
core
with
excellent
chemo-,
regio-,
diastereoselectivity.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(19), С. 13977 - 13994
Опубликована: Сен. 11, 2023
The
combination
of
the
Ugi
reaction
and
electro-organic
synthesis
can
aid
in
creation
novel
heterocycles
that
have
not
been
previously
explored.
In
this
study,
a
new
strategy
utilizing
bis-amides
from
has
developed,
which
produce
C–S,
C–Se,
C–C═O
functionalized
five-membered
spirolactams
mediated
by
electricity
under
catalyst-
metal-free
conditions.
Notably,
approach
be
applied
using
microelectro-flow
reactor
(μ-EFR)
for
gram-scale
synthesis.
described
synthesize
complex
azaspiro-fused
tricyclic
scaffolds
with
high
diastereo-
regioselectivity,
highlighting
its
versatility
potential.
