Advanced Synthesis & Catalysis,
Год журнала:
2020,
Номер
362(9), С. 1724 - 1818
Опубликована: Янв. 20, 2020
Abstract
Phosphorus‐substituted
heterocycles
represent
an
important
class
of
organophosphorus
compounds,
which
not
only
widely
exist
in
biologically
active
pharmaceuticals,
agrochemicals,
but
also
have
widespread
applications
material
science
and
organic
synthesis
as
ligands
for
transition
metal
complexes.
The
such
compounds
integrates
the
development
new
synthetic
methods
exploration
efficient
catalytic
systems,
reflects
latest
achievements
organic,
metal,
photo
even
electrochemical
catalysis,
facilitates
sufficient
quantities
related
potential
medicinal
agents
biological
probes
this
area.
Over
past
few
decades,
two
major
strategies
been
established
toward
phosphorus‐substituted
heterocycles.
This
review
summarizes
recent
progress
field
discusses
reaction
mechanisms
detail.
advantages
limitations
each
subdivisional
tactic
are
presented,
opportunities
still
open
outlined.
magnified
image
Angewandte Chemie International Edition,
Год журнала:
2021,
Номер
60(27), С. 14921 - 14930
Опубликована: Март 17, 2021
Abstract
A
highly
enantiodivergent
organocatalytic
method
is
disclosed
for
the
synthesis
of
atropisomeric
biaryls
via
kinetic
resolution
inspired
by
a
dipeptide‐phosphonium
salt‐catalyzed
Atherton–Todd
(A‐T)
reaction.
This
flexible
approach
led
to
both
R
‐
and
S
‐enantiomers
fine‐tuning
bifunctional
phosphonium
with
excellent
selectivity
factors
(
s
)
up
1057
525,
respectively.
The
potential
newly
synthesized
O‐phosphorylated
biaryl
diols
was
illustrated
axially
chiral
organophosphorus
compounds.
Mechanistic
investigations
suggest
that
halide
catalyst
differentiates
between
in‐situ‐generated
P‐species
in
A‐T
process,
mainly
involving
phosphoryl
chloride
phosphoric
anhydride,
thus
leading
O‐phosphorylation
reactions.
Furthermore
hydrogen
bonding
interactions
catalysts
phosphorus
molecules
were
crucial
asymmetric
induction.
Organic Letters,
Год журнала:
2021,
Номер
23(5), С. 1541 - 1547
Опубликована: Фев. 24, 2021
A
Tf2O/DMSO-based
system
for
the
dehydrogenative
coupling
of
a
wide
range
alcohols,
phenols,
thiols,
and
thiophenols
with
diverse
phosphorus
reagents
has
been
developed.
This
metal-
strong-oxidant-free
strategy
provides
facile
approach
to
great
variety
organophosphinates
thiophosphates.
The
simple
reaction
system,
good
functional-group
tolerance,
broad
substrate
scope
enable
application
this
method
modification
natural
products
direct
synthesis
bioactive
molecules
flame
retardants.
Organic Letters,
Год журнала:
2020,
Номер
22(8), С. 3062 - 3066
Опубликована: Апрель 7, 2020
We
report
a
direct
and
green
electrochemical
oxidative
cross-dehydrogenative
coupling
reaction
of
N-heterocycles
with
hydrogen
phosphoryl
compounds
under
external
oxidant-free
conditions.
Various
phosphorylation
products
substituted
carbazoles
indoles
are
assembled
in
modest
to
excellent
yields.
A
release
process
is
preliminarily
demonstrated
H2
the
sole
byproduct.
An
imidazolium
based
ionic
liquid
selected
as
optimal
electrolyte.
Chemical Synthesis,
Год журнала:
2021,
Номер
unknown
Опубликована: Янв. 1, 2021
Chemical
Synthesis
is
an
open
access
peer-reviewed
journal
publishing
original
research
involving
all
areas
of
the
chemical
sciences.
The
aims
to
be
premier
resource
seminal
and
insightful
showcases
for
researchers
in
both
academia
industry,
providing
a
platform
inspiration
future
chemistry.
intends
serve
as
preeminent
international
chemistry
has
ambition
among
first
choices
chemists
publication
their
discoveries.
ACS Catalysis,
Год журнала:
2021,
Номер
11(22), С. 13902 - 13912
Опубликована: Ноя. 1, 2021
Sulfur-stereogenic
sulfoximines
particularly
with
a
free
N-H
unit
exhibit
intriguing
chemical
and
biological
activities,
thus
have
received
continuous
attention
from
chemists.
However,
there
are
currently
no
examples
of
guiding
catalytic
asymmetric
strategies
available
to
directly
access
these
molecules.
Herein,
we
disclose
an
efficient
practical
protocol
for
the
direct
enantioenrichment
sulfoximines,
via
bifunctional
phosphonium
salt-catalyzed
desymmetrization
triggered
by
Atherton–Todd
reaction
together
further
extended
nucleophilic
acyl
substitution-type
reaction.
A
series
bearing
assortment
aromatic
groups
(70
examples)
tolerated
in
this
incidentally
involving
minority
kinetic
resolution
(KR).
The
desymmetrized
products
can
be
easily
transformed
into
chiral
sulfoxides
other
classes
active
sulfur-stereogenic
compounds.
Mechanistic
studies
provided
insights
pathway
suggesting
desymmetrization/KR
synergic
process,
also
offered
support
on
hydrogen-bonding
interactions
as
key
elements
successful
stereocontrol.
Organic Letters,
Год журнала:
2020,
Номер
22(12), С. 4742 - 4748
Опубликована: Июнь 2, 2020
Addition
of
P-H
species
to
carbonyl
groups,
namely
the
Pudovik
reaction,
normally
delivers
hydroxyl
phosphorus
compounds,
along
with
phosphate
byproducts
in
some
cases.
A
few
controllable
systems
starting
from
phosphites
were
set
up
mainly
provide
phosphates.
Herein,
we
present
a
highly
selective
protocol
phosphonate
precursors
leading
phosphinate
derivatives.
Enantioenriched
phosphinates
successfully
achieved
chiral
phosphine
oxide
precursors.
Experimental
and
theoretical
investigations
conducted
understand
mechanistic
details.
Organic Letters,
Год журнала:
2020,
Номер
22(15), С. 6143 - 6149
Опубликована: Июль 10, 2020
We
report
a
redox-neutral
P(O)–N
coupling
reaction
of
P(O)–H
compounds
with
azides
via
photoredox
and
copper
catalysis,
providing
new
access
to
useful
phosphinamides,
phosphonamides,
phosphoramides.
This
transformation
tolerates
wide
range
nucleophilic
functionalities
including
alcohol
amine
nucleophiles,
which
makes
up
for
the
deficiency
classical
nitrogen
substitution
reactions.
As
demonstration
broad
potential
applications
this
methodology,
late-stage
functionalization
diverse
array
azido-bearing
natural
products
drug
molecules,
preliminary
asymmetric
reaction,
continuous
visible-light
photoflow
process
have
been
developed.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(11), С. 7848 - 7858
Опубликована: Май 29, 2024
A
CuH-catalyzed
reductive
coupling
of
nitroarenes
with
phosphine
oxides
is
developed,
which
produces
a
series
phosphamides
in
moderate
to
excellent
yields
good
functional
group
tolerance.
Gram-scale
synthesis
and
late-stage
modification
nitro-aromatic
molecule
niclosamide
are
also
successfully
conducted.
The
mechanism
study
shows
that
the
nitro
transformed
after
being
reduced
nitroso
nucleophilic
addition
procedure
involved
during
reaction.
