Visible Light-Promoted Aromatization-Driven Deconstructive Fluorination of Spiro Carbocycles
Wenpeng Yang,
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Hong-Jie Miao,
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Le Liu
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(35), P. 7442 - 7446
Published: Aug. 26, 2024
A
visible
light-promoted
aromatization-driven
deconstructive
fluorination
of
spiro
carbocycles
is
presented.
series
dihydroquinazolinones
reacted
efficiently
with
NFSI
under
light
irradiation
to
afford
the
2-(4-fluoroalkyl)quinazolin-4(3H)-ones
in
good
yields
excellent
functional
group
tolerance.
radical
pathway
involving
C–C
bond
cleavage
and
F
atom
transfer
proposed
for
reaction.
In
addition,
ring-opening
chlorination
NCS
was
also
applicable.
Language: Английский
Hydride Transfer-Enabled Dearomative Spirocyclization of Isoxazoles with O-Alkyl ortho-Oxybenzaldehydes
Lianyi Cao,
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Shihai Yan,
No information about this author
Fangzhi Hu
No information about this author
et al.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 17, 2025
The
TfOH-catalyzed
dearomative
[5
+
1]
annulations
were
developed
for
the
construction
of
chromane-fused
spiroisoxazolines
from
readily
available
5-amino-isoxazoles
and
O-alkyl
ortho-oxybenzaldehydes.
"two-birds-with-one-stone"
strategy
featuring
dearomatization
α-C(sp3)–H
bond
functionalization
oxygen
was
disclosed
via
a
cascade
condensation/[1,5]-hydride
transfer/dearomative
spirocyclization
process.
In
addition,
unprecedented
direct
isoxazoles
achieved,
which
introduced
new
family
member
chemistry.
Language: Английский
Construction of C–S and C–Se Bonds via Photocatalytic Aromatization-Driven Deconstructive Diversification of Spiro-Dihydroquinazolinones Derived from Unstrained Ketones
Tao Wang,
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Jin‐Long Dai,
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Yifeng Jiang
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et al.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 13, 2025
A
novel
and
robust
deconstructive
functionalization
reaction
of
spiro-dihydroquinazolinones
with
sulfenylating
reagents
in
the
presence
base
has
been
realized
under
visible
light
irradiation.
This
enabled
direct
ring-opening
unstrained
cyclic
ring
systems,
producing
skeletally
diverse
functionalized
quinazolinones
moderate
to
good
yields.
range
variety
including
diaryl
disulfide,
thiosulfonate,
dithiosulfonate
1-[(trifluoromethyl)thio]-2,5-pyrrolidinedione
were
compatible
for
this
transformation.
In
addition,
diselenide
selenosulfonate
could
also
couple
form
C-Se
Bonds.
Mechanistic
studies
revealed
that
proceeds
via
a
radical-radical
coupling
pathway.
Language: Английский
Aerobic alcoholization via aromatization driven C–C bond cleavage of unstrained ketones
Green Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
A
novel
aerobic
aldolization
approach
that
employs
aromatization-driven
C–C
bond
cleavage
for
the
deacetylation
of
unstrained
ketones
was
reported.
Various
primary
and
secondary
alcohols
were
generated
under
oxygen
atmosphere
without
any
catalysts.
Language: Английский
Regioselective C-C bond cleavage/aminocarbonylation cascade under copper catalysis
Qi-Chao Shan,
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Zhao Yan,
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Yong Wu
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et al.
Science China Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Aug. 28, 2024
Language: Английский
Photoinduced Aromatization-Driven Deconstructive Fluorosulfonylation of Spiro Dihydroquinazolinones
Wenpeng Yang,
No information about this author
Hong-Jie Miao,
No information about this author
Gang Wang
No information about this author
et al.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 30, 2024
A
catalyst-free
photoinduced
deconstructive
fluorosulfonylation
cascade
of
spiro
dihydroquinazolinones
with
DABSO
and
NFSI
is
reported.
This
protocol
features
mild
reaction
conditions,
good
yields
excellent
functional
group
tolerance,
providing
a
practical
approach
to
the
quinazolin-4(1H)-one-functionalized
aliphatic
sulfonyl
fluorides.
In
addition,
ease
gram-scale
synthesis
versatility
SuFEx
exchange
highlight
application
potential
this
protocol.
Language: Английский