Synthesis,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 5, 2024
Abstract
Diazophosphonates
function
as
indispensable
synthetic
intermediates
within
the
domain
of
organic
chemistry,
serving
precursors
for
a
diverse
range
molecules,
with
potential
applications
bioactive
compounds.
α-Diazomethylphosphonates
showcase
expansive
reactivity
and
elevated
levels
enantioselectivity
in
asymmetric
transformations,
especially
conjunction
suitable
catalyst
systems.
This
review
compiles
latest
advancements
diazophosphonate
chemistry
from
2016
to
2024,
highlighting
their
transformative
synthesis.
Diazophosphonates,
regarded
revolutionary
compounds,
exhibit
unique
attributes
carbene
precursors,
driving
chemical
reactions
such
[3+2]
cycloaddition,
[3+3]
substitution
reactions.
Their
adaptability
functional
group
conversions
underscores
pivotal
role
various
methodologies.
The
highlights
growing
interest
among
chemists,
fostering
novel
strategies
expanding
application
horizons.
multifaceted
utility
diazophosphonates
reagents,
intermediates,
catalysts
significance
modern
pharmaceutical
applications,
prompting
further
exploration
into
this
dynamic
field.
1
Introduction
2
Cycloaddition
Reactions
3
Asymmetric
4
5
Substitution
6
Carbene
Precursors
7
Chemistry
Fluorinated
Compounds
8
Other
9
Future
Directions
10
Conclusion
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(12), P. 1969 - 1974
Published: April 30, 2022
Abstract
We
report
a
one‐pot
reaction
of
(β‐amino‐α,α‐difluoroethyl)phosphonates
involving
aza‐Wittig
reagents,
in
which,
difluoromethylphosphonate‐containing
diazo
and
trifluoromethylated
ketones
assemble
to
furnish
azo‐containing
α‐fluorovinylphosphonates.
Mechanism
studies
disclose
pathway,
which
contains
an
reaction,
water
addition
hydrazone,
C−F
bond
cleavage
with
reagent
as
key
intermediate.
This
is
conducted
at
60
°C
affording
series
α‐fluorovinylphosphonate
compounds
42–94%
yields
Z
‐stereoselectivity.
work
opens
vision
for
the
difluoroalkyl‐substituted
diazos,
provides
strategy
synthesis
derivatives.
magnified
image
Beilstein Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
19, P. 541 - 549
Published: April 25, 2023
A
synthetic
route
to
the
bench-stable
fluorinated
masked
carbene
reagent
diethyl
2-diazo-1,1,3,3,3-pentafluoropropylphosphonate,
bearing
a
trifluoromethyl
and
difluoromethyl
group
is
reported
for
first
time.
Its
application
in
CuI-catalyzed
cyclopropanation
reactions
with
aromatic
aliphatic
terminal
alkenes
under
mild
reaction
conditions
demonstrated.
In
total,
sixteen
new
cyclopropanes
were
synthesized
good
very
yields.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(16), P. 11874 - 11884
Published: Aug. 3, 2023
A
direct
arylsulfonylation
of
β,γ-unsaturated
hydrazones
method,
in
which
sulfonated
pyrazolines
are
accessed
by
a
three-component
reaction
hydrazones,
DABSO,
and
aryldiazonium
tetrafluoroborates,
has
been
developed
without
external
oxidants
or
catalysts.
This
transformation
is
triggered
the
formation
arylsulfonyl
radicals
situ
from
tetrafluoroborates
enabled
controllable
generation
C
center
radical,
DABSO
was
utilized
as
sulfone
source
an
oxidant
this
radical-mediated
cascaded
reaction.
wide
range
substrates
can
be
applied
process
to
afford
good
yield,
it
amenable
for
gram-scale
synthesis.
Royal Society of Chemistry eBooks,
Journal Year:
2024,
Volume and Issue:
unknown, P. 109 - 231
Published: Feb. 21, 2024
This
chapter
shows,
as
in
previous
years,
the
most
important
achievements
of
2021
year
area
organo-phosphorus
compounds
containing:
three
P–O
bonds
(Section
2:
phosphoric
acids
and
their
derivatives),
two
one
P–C
3:
phosphonic
derivatives)
well
4:
phosphinic
addition
to
phosphoryl
group
P═O,
present
all
groups
compounds.
Each
main
sections
covers
“synthesis
reactions”
including
pure
synthesis
without
applications,
biological
applications”
miscellaneous
directed
towards
non-biological
applications.
At
end
each
subsection,
corresponding
are
shown
for
hetero-analogues
which
phosphorus–oxygen
have
been
replaced
by
phosphorus–heteroatom
P–X
and/or
P═Y
(X,
Y
=
N,
S
or
Se).
The
subsection
on
quinquevalent
phosphorus
derivatives
catalysts
has
placed,
usual,
at
entire
chapter,
after
a
review
As
devoted
dominated
over
smaller
section
derivatives,
literature
references
these
remained
ratio
4
:
12
1.
A
dynamic,
five-fold
increase
number
works,
subject
chiral
catalysts,
recorded
this
year.
