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
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(14), P. 2630 - 2635
Published: March 30, 2022
A
series
of
indole-derived
alkenes
have
been
designed
and
applied
in
a
photocatalytic
cascade
reaction
with
bromodifluoroacetate
esters,
affording
an
unknown
type
tetracyclic
tetrahydro-γ-carboline
derivative
up
to
90%
yields.
Mechanistic
studies
suggest
that
the
proceeds
as
key
intermediate.
The
tolerates
diverse
pool
substrates,
which
provides
efficient
method
for
construction
compounds.
Beilstein Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
20, P. 212 - 219
Published: Feb. 2, 2024
An
efficient
multicomponent
reaction
of
newly
designed
β-trifluoromethyl
β-diazo
esters,
acetonitrile,
and
carboxylic
acids
via
an
interrupted
esterification
process
under
copper-catalyzed
conditions
has
been
developed,
which
affords
various
unsymmetrical
N
,
-diacyl-β-amino
esters
in
good
to
excellent
yields.
The
features
mild
conditions,
a
wide
scope
β-amino
acids,
also
applicability
large-scale
synthesis,
thus
providing
way
for
the
synthesis
β-diacylamino
esters.
Furthermore,
this
represents
first
example
Mumm
rearrangement
Chemical Reviews,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 22, 2025
Fluorine
and
nitrogen
form
a
successful
partnership
in
organic
synthesis,
medicinal
chemistry,
material
sciences.
Although
fluorine-nitrogen
chemistry
has
long
rich
history,
this
field
received
increasing
interest
made
remarkable
progress
over
the
past
two
decades,
driven
by
recent
advancements
transition
metal
organocatalysis
photochemistry.
This
review,
emphasizing
contributions
from
2015
to
2023,
aims
update
state
of
art
synthesis
applications
nitrogen-based
organofluorine
functional
molecules
chemistry.
In
dedicated
sections,
we
first
focus
on
fluorine-containing
reagents
organized
according
type
groups
attached
nitrogen,
including
N-F,
N-RF,
N-SRF,
N-ORF.
review
also
covers
nitrogen-linked
building
blocks,
catalysts,
pharmaceuticals,
agrochemicals,
underlining
these
components'
broad
applicability
growing
importance
modern
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(11), P. 2258 - 2263
Published: March 17, 2022
A
method
for
the
generation
of
trifluoromethylated
β-keto
diazos
and
their
applications
in
intramolecular
Appel
type
reactions
are
reported.
The
key
success
this
reaction
is
a
diazo
species
as
an
N-nucleophile
reactions.
This
conducted
under
mild
conditions
has
broad
substrate
scope,
affording
trifluoromethylpyrazoles
≤94%
yields.
protocol
represents
new
also
mode
fluoro
diazoalkanes.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(43), P. 8036 - 8040
Published: Oct. 26, 2022
A
Ru-catalyzed
reaction
of
difluoroalkyl
diazo
compounds
with
Hantzsch
ester
under
visible
light
to
achieve
the
formation
α-fluorovinylphosphonates
via
a
radical
process
has
been
developed.
Mechanistic
experiments
and
density
functional
theory
calculations
reveal
that
generation
carbon
is
directly
through
hydrogen
atom
transfer
(HAT)
by
ester.
This
system
represents
first
example
radicals
from
Hantzsch-ester-assisted
HAT
also
demonstrates
new
radical-involved
pathway
for
compounds.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(8), P. 1948 - 1958
Published: Jan. 1, 2023
The
mechanism
and
stereoselectivity
of
the
Ni-catalyzed
[3
+
3]
annulation
between
donor–acceptor
cyclopropanes
(DACs)
diaziridines
were
rationalized
by
DFT
calculations.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(17), P. 2883 - 2887
Published: July 21, 2023
Abstract
(β‐Diazo‐α,α‐difluoroethyl)phosphonates
have
been
emerging
as
useful
building
blocks
in
organic
synthetic
chemistry
recent
years,
which
can
be
used
diazo
analog
or
masked
carbene
for
the
rapid
assembly
of
difluoromethylene
phosphonate‐containing
compounds.
Herein,
we
elaborate
a
method
synthesis
α‐fluoro‐β‐ketophosphonates
from
hydration/C−F
bond
cleavage
situ
generated
(β‐amino‐α,α‐difluoroethyl)phosphonates
via
Rh‐carbene
intermediate.
Divers
are
tolerated
this
reaction
affording
good
yields.
This
water
coupling
partner,
represents
(β‐diazo‐α,α‐difluoroethyl)phosphonates
and
also
generating
bioactive
α‐fluoro‐β‐ketophosphonates.
