Asian Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
11(8)
Published: July 2, 2022
Abstract
A
facile
and
efficient
method
for
the
synthesis
of
α
‐diarylmethyl
substituted
phenols
from
para
‐quinone
methides
(
p
‐QMs)
with
has
been
developed
by
using
phosphoric
acid
as
catalyst
water
green
solvent
under
mild
conditions.
In
addition,
when
TEMPO
was
added
an
additive
reaction,
diaryl‐substituted
could
be
generated
target
product.
The
reactions
show
high
functional
group
tolerance,
good
to
excellent
yields
unique
selectivity,
a
broad
range
motif
containing
phenol(s)
quinones
prepared
through
divergent
methods.
Furthermore,
series
control
experiments
were
performed
gain
insights
plausible
mechanisms.
These
protocols
have
atomic
economy,
may
significant
implications
construction
C(
sp
3
)−C(
2
)
bonds
in
organic
synthesis.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 3, 2025
A
synthetic
strategy
of
a
palladium-catalyzed
cascade
annulation
reaction
followed
by
aerial
oxidation
was
designed
to
construct
6H-benzo[c]chromene
scaffolds.
Various
6H-benzo[c]chromenes
were
synthesized
under
mild
conditions
using
easily
accessible
p-QMs
and
commercially
available
o-hydroxyarylboronic
acids.
One
the
chromenes
has
been
ambiguously
confirmed
single-crystal
XRD
analysis.
Interestingly,
our
could
be
transformed
into
valuable
6H-benzo[c]chromen-6-ones
via
oxidation.
The Chemical Record,
Journal Year:
2021,
Volume and Issue:
21(12), P. 4150 - 4173
Published: Aug. 9, 2021
In
the
last
few
years,
there
has
been
an
explosive
growth
in
area
of
para-quinone
methide
(p-QM)
chemistry.
This
boom
is
actually
due
to
unique
reactivity
pattern
p-QMs,
and
also
their
remarkable
synthetic
applications.
fact,
p-QMs
serve
as
synthons
for
unsymmetrical
diaryl-
triarylmethanes,
construction
diverse
range
carbocycles
heterocycles.
a
wide
structurally
complex
heterocyclic
frameworks
could
be
accessed
through
transformations
modified
stable
p-QMs.
Therefore,
main
focus
this
review
article
cover
recent
advancements
transition-metal,
Lewis
acid
base-catalyzed/mediated
p-quinone
methides
(p-QMs)
oxygen-
nitrogen-containing
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(9), P. 1290 - 1331
Published: Feb. 28, 2023
Abstract
Functionalized
4
H
‐chromenes
represent
one
class
of
the
most
important
structural
scaffolds
in
both
synthetic
and
medicinal
chemistry.
They
often
appear
an
arrange
biological
natural
products,
pharmaceutical
agents
drug
candidates.
The
significance
has
stimulated
development
efficient
methodologies
for
synthesis
such
compounds.
In
this
review,
a
comprehensive
discussion
on
different
approaches
to
been
presented
with
emphasis
reaction
features
mechanisms.
Three
main
categories
are
outlined:
1)
nucleophilic
addition
2
‐chromene
derivatives,
2)
ring
formation
involved
cycloaddition
or
cyclization
reactions,
3)
miscellaneous
reactions.
magnified
image
Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
363(20), P. 4667 - 4694
Published: Aug. 28, 2021
Abstract
As
an
important
branch
of
the
Michael
addition
reaction,
aza‐Michael
cascade
reaction
has
been
developed
rapidly
in
recent
years.
This
is
because
serves
as
method
for
effectively
constructing
functionalized
C−N
bonds,
which
can
be
widely
used
synthesis
chiral
drugs
and
their
intermediates
natural
products.
Given
importance
this
topic,
review
highlights
developments
triggered
reactions
asymmetric
synthesis,
including
aza‐Michael/Michael,
aza‐Michael/Aldol,
aza‐Michael/Henry,
aza‐Michael/hemiacetal,
aza‐Michael/Mannich,
aza‐Michael/alkylation,
aza‐Michael/cyclization,
aza‐Michael/ring‐opening,
aza‐Michael‐IED/HAD,
aza‐Michael/INCR,
aza‐Michael/1,6‐conjugate
reactions.
In
paper,
mechanism
derivatization
experiments
different
are
timely
introduced
to
provide
a
more
comprehensive
theoretical
basis
subsequent
studies.
magnified
image
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(2), P. 1516 - 1527
Published: Jan. 7, 2021
A
simple
and
efficient
method
for
the
regioselective
thiolation
of
p-quinone
methides
with
sodium
aryl/alkyl
sulfinates
has
been
established
using
an
acid/phosphine-induced
radical
route
under
transition-metal-free
conditions.
broad
range
(p-QMs)
are
compatible
reaction,
giving
expected
products
good
to
excellent
yields.
Control
experiments
were
also
performed
gain
insights
into
generation
mechanism
thiyl
radicals
hydrogen-atom
transfer
process.
This
protocol
provides
a
safe
feasible
way
formation
carbon–sulfur
bonds.
Green Synthesis and Catalysis,
Journal Year:
2021,
Volume and Issue:
3(1), P. 53 - 58
Published: Oct. 22, 2021
A
new
DBU-catalyzed
formal
[4
+
2]
cycloaddition
between
ortho-hydroxyphenyl-substituted
para-quinone
methides
and
electron-deficient
dienophiles
including
3-methyleneoxindoles
2-aryldeneindene-1,3-diones
was
established.
wide
range
of
functionalized
spiro[chromane-3,3′-indolines]
spiro[chromane-3,2′-indenes]
were
successfully
synthesized
in
good
yields
with
high
diastereoselectivity.
The
features
the
reaction
included
readily
available
substrates,
mild
conditions,
convenient
methodology
functional
group
tolerance.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(15), P. 10129 - 10139
Published: July 15, 2021
We
have
reported
an
efficient
and
metal-free
method
for
the
construction
of
α-diarylmethine
imino
sulfanone
using
acid-catalyzed
1,6-conjugate
addition
sulfoximines
on
para-quinine
methides
(p-QMs).
This
showed
broad
functional
group
tolerance
a
wide
range
substrate
scope
with
good
to
excellent
yield.
The
protocol
exhibits
mild
reaction
conditions
high
atom
economy.
practicability
present
was
supported
by
Gram-scale
reaction.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(15), P. 5885 - 5890
Published: July 19, 2021
A
new
tandem
annulation
of
p-quinone
methides
(p-QMs)
with
ynamides
is
described.
This
cascade
reaction
features
a
unique
combination
(2
+
2)
annulation,
retro-4π
electrocyclization,
and
imino-Nazarov
cyclization,
wherein
vinyl
(p-VQMs)
as
one
the
key
intermediates
have
been
identified
chemically.
Significantly,
an
unusual
structural
reconstruction
p-QMs
involving
cleavage
C5–C6
bond
late-stage
formation
C4–C6
involved,
leading
to
methodology
development
for
construction
functionalized
aminoindenes.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(21), P. 14983 - 15003
Published: Oct. 19, 2021
A
simple
and
efficient
method
for
the
silver-catalyzed
regioselective
phosphorylation
of
para-quinone
methides
(p-QMs)
with
P(III)-nucleophiles
(P(OR)3,
ArP(OR)2,
Ar2P–OR)
has
been
established
via
Michaelis–Arbuzov-type
reaction.
broad
range
are
well
tolerated
under
mild
conditions,
giving
expected
diarylmethyl-substituted
organophosphorus
compounds
good
to
excellent
yields.
Moreover,
a
series
corresponding
enantiomers
can
be
obtained
by
employing
dialkyl
arylphosphonite
(ArP(OR)2)
as
substrates.
The
control
experiments
31P
NMR
tracking
were
also
performed
gain
insights
plausible
reaction
mechanism.
This
protocol
may
have
significant
implications
formation
C(sp3)–P
bonds
in
reactions.
