Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 29, 2024
Abstract
The
C3‐alkenylation
of
indoles
have
been
developed
by
means
a
novel
in
situ
iodination
tactic
which
is
capable
mediating
the
Heck
coupling
with
alkenes.
method
features
specific
site‐selectivity
oriented
C−I
bond,
high‐step
efficiency
without
pre‐functionalization
for
C‐halogen
bond
construction,
as
well
highly
general
tolerance
to
different
terminal
alkenes,
including
unactivated
acrylates,
acrylic
acid,
vinyl
sulfone
functionalized
natural
products.
Chemical Communications,
Год журнала:
2023,
Номер
59(27), С. 4036 - 4039
Опубликована: Янв. 1, 2023
The
synthesis
of
N-naphthyl
pyrazoles
has
been
realized
by
the
direct
three-component
reactions
enaminones,
aryl
hydrazine
hydrochlorides
and
internal
alkynes
via
Rh(III)
catalysis.
synthetic
employing
simple
substrates
lead
to
simultaneous
construction
dual
cyclic
moieties,
including
a
pyrazole
ring
phenyl
ring,
sequential
formation
two
C-N
three
C-C
bonds.
Chemical Communications,
Год журнала:
2023,
Номер
59(33), С. 4872 - 4890
Опубликована: Янв. 1, 2023
Recent
advances
in
the
direct
synthesis
of
trifluoromethyl-containing
heterocycles
from
trifluoroacetimidoyl
chlorides
(TFAICs)
and
derivatives,
including
trifluoroacetimidohydrazides
(TFAIHs)
CF3-imidoyl
sulfoxonium
ylides
(TFISYs),
are
systematically
summarized
discussed.
The
cascade
annulation
reactions
synthons
with
suitable
coupling
partners
have
emerged
as
a
powerful
promising
tool
for
construction
variety
trifluoromethyl-substituted
heterocycles.
Compared
other
building
blocks,
TFAICs
derivatives
notable
merits
easy
availability
handling,
relative
stability
safety,
high
reactivity.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(15), С. 3843 - 3848
Опубликована: Янв. 1, 2023
We
have
developed
a
Rh(
iii
)-catalyzed
C–H
activation/chemodivergent
annulation
of
N
-carbamoylindoles
with
TFISYs,
allowing
facile
access
to
variety
trifluoromethyl-substituted
(dihydro)pyrimidoindolones
high
efficiency.
Solvents
play
critical
role
in
the
selectivity
reaction.
Organic Letters,
Год журнала:
2024,
Номер
26(1), С. 62 - 67
Опубликована: Янв. 3, 2024
We
have
found
a
chameleonic
reactivity
of
imidoyl
sulfoxonium
ylides.
On
the
one
hand,
ylides
react
with
electron-deficient
reagents,
such
as
alkynyl
esters,
to
lead
formation
1,2-dihydro-pyridines.
The
methyl
group
attached
sulfur
atom
acts
methylene
donor.
other
pyridinium
1,4-zwitterionic
thiolates,
which
leads
functionalized
pyrroles.
Both
transformations
feature
mild
reaction
conditions
and
good
functional
tolerance.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(9), С. 1521 - 1525
Опубликована: Март 31, 2023
Abstract
An
approach
for
the
construction
of
5‐trifluoromethyl‐1,4‐dihydro‐1,2,4‐triazines
has
been
developed
via
base‐mediated
[3+3]
cycloaddition
in‐situ
generated
nitrile
imines
and
CF
3
‐substituted
imidoyl
sulfoxonium
ylides.
The
metal‐free
protocol
is
characterized
by
readily
available
starting
materials,
mild
conditions,
a
broad
substrate
scope,
high
efficiency,
good
synthetic
prospect,
scalability.
magnified
image
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(19), С. 3382 - 3386
Опубликована: Авг. 16, 2023
Abstract
A
heating‐induced
desulfuration
annulation
of
pyridinium
1,4‐zwitterionic
thiolates
and
CF
3
‐substituted
imidoyl
sulfoxonium
ylides
has
been
achieved,
allowing
a
route
to
biologically
important
5‐trifluoromethylpyrroles.
The
transformation
proceeds
through
an
unusual
((3+3)‐1)
pathway
under
metal‐free
conditions
with
the
extrusion
4‐methoxypyridine,
sulfur
DMSO.
scale‐up
reaction
further
obtained
pyrrole
products
have
performed
demonstrate
synthetic
utility
developed
method.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(22), С. 3855 - 3860
Опубликована: Окт. 18, 2023
Abstract
A
rhodium(III)‐catalyzed
C−H
activation/[4+1]
annulation
of
2‐aryl‐3
H
‐indoles
and
CF
3
‐substituted
imidoyl
sulfoxonium
ylides
(TFISYs)
has
been
achieved,
producing
a
wide
variety
trifluoroacetimidoyl‐substituted
11
‐isoindolo[2,1‐a]indoles
in
51–86%
yields.
The
cascade
reaction
involves
imidoylmethylation,
tautomerization
AgOAc‐mediated
C−N
bond
formation
sequence.
could
be
scaled
up
to
2
mmol
scale.
Chinese Journal of Chemistry,
Год журнала:
2023,
Номер
41(23), С. 3205 - 3210
Опубликована: Июль 17, 2023
Comprehensive
Summary
A
thermally‐induced
multi‐component
reaction
of
CF
3
‐substituted
imidoyl
sulfoxonium
ylides
(TFISYs),
amines
and
(triphenylphosphonio)difluoroacetate
(PDFA)
has
been
developed,
allowing
a
facile
access
to
2‐trifluoromethyl‐4‐aminoquinolines
in
high
yields.
The
proceeds
smoothly
with
or
without
the
addition
sulfur
utilizes
difluorocarbene
as
C1
synthon
under
simply
heating
conditions.
Mechanistic
study
reveals
that
in‐situ
generated
thiocarbonyl
fluoride,
isothiocyanate
gem
‐difluoroalkene
might
act
key
intermediates.
Organic Letters,
Год журнала:
2023,
Номер
25(38), С. 7046 - 7050
Опубликована: Сен. 18, 2023
A
base-mediated
cascade
reaction
of
CF3-imidoyl
sulfoxonium
ylides
and
azo
compounds
has
been
achieved,
allowing
for
facile
access
to
trifluoromethyl-substituted
1,2-dihydroquinoxalines
diimines
in
moderate
excellent
yields.
Noteworthy
is
that
the
unusual
N-N
bond
cleavage
rearrangement
are
involved
transformations.
