Encyclopedia of Reagents for Organic Synthesis,
Journal Year:
2021,
Volume and Issue:
unknown, P. 1 - 17
Published: April 30, 2021
XPhos
[564483-18-7]
C33H49P
(MW
476.72)
InChI
=
1S/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3
InChIKey
UGOMMVLRQDMAQQ-UHFFFAOYSA-N
(bulky,
electron-rich
monophosphine
used
as
ligand
in
transition-metal-catalyzed
reactions,
especially
the
context
of
Pd
chemistry)
Alternative
Names:
2-dicyclohexylphosphino-2′,4′,6′-triisopropyl
biphenyl,
XPhos.
Physical
Data:
mp
187–190
°C.
Solubility:
soluble
most
organic
solvents.
Form
Supplied
in:
white
solid;
widely
available.
t-BuXPhos
[564483-19-8]
C29H45P
424.65)
1S/C29H45P/c1-19(2)22-17-24(20(3)4)27(25(18-22)21(5)6)23-15-13-14-16-26(23)30(28(7,8)9)29(10,11)12/h13-21H,1-12H3
SACNIGZYDTUHKB-UHFFFAOYSA-N
Pd-catalyzed
reactions)
2-di-t-butylphosphino-2′,4′,6′-triisopropyl
t-BuXPhos,
di-t-BuXPhos.
148–151
Handling,
Storage,
and
Precautions:
oxidation
these
related
phosphines
has
been
examined.1
The
presence
three
isopropyl
groups
on
2′,
4′,
6′
positions
nonphosphine-containing
ring
reduces
their
reactivity
toward
atmospheric
oxygen
to
less
than
3%
at
room
temperature
toluene
solution
after
65
h.
Under
an
atmosphere
O2
100
°C
for
h
only
28%
13%
phosphine
oxide
are
formed
from
tert-BuXPhos,
respectively.
Preparative
Method:
can
be
prepared
by
reaction
2-bromochlorobenzene
with
Grignard
reagent
1-bromo-2,4,6-triisopropylbenzene
THF,
followed
addition
catalytic
CuCl
ClPCy2.
A
similar
procedure
using
CIPtBu2
was
applied
synthesis
t-BuXPhos.2
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(18), P. 7068 - 7072
Published: Jan. 1, 2023
A
new
catalyst-,
metal-
and
additive-free
green
strategy
to
synthesize
bis-substituted
sulfoxonium
ylides
is
reported,
which
has
good
compatibility
with
various
substituents
generally
excellent
yields.
Asian Journal of Organic Chemistry,
Journal Year:
2020,
Volume and Issue:
9(7), P. 1032 - 1035
Published: May 25, 2020
Abstract
A
visible‐light‐catalyzed
radical
N
‐acylation
of
amines
with
carboxylic
acids
was
achieved
by
means
eosin
Y
as
the
photocatalyst
under
aqueous
medium
without
any
transition‐metal‐based
catalytic
systems.
The
new
method
takes
advantages
visible‐light
photocatalysis
to
generate
amides
mild
conditions.
variety
have
been
synthesized
in
good
excellent
yields.
Moreover,
strategy
successfully
applied
preparation
paracetamol.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(27)
Published: April 29, 2024
Abstract
Sulfo(xo)nium
diacylmethylides
(sulfur
ylides)
are
simple,
stable,
readily
prepared,
and
versatile
synthons.
Compared
with
the
sulfo(xo)nium
monoacylmethylides,
they
can
be
compatible
more
rigorous
reaction
conditions
showcase
unique
characteristics
due
to
their
excellent
stability.
This
concept
article
provides
an
account
for
syntheses
of
diacylmethylides,
including
utilization
active
methylene
compounds,
carbene
precursors,
electron‐deficient
alkynes
as
substrates,
discussions
on
substrate
scopes,
proposed
mechanisms,
selected
product
examples,
applications.
Challenges
further
exploration
prospect
in
future
also
suggested.
Nature Communications,
Journal Year:
2024,
Volume and Issue:
15(1)
Published: Nov. 25, 2024
α-Functionalized
Si-,
Ge-,
B-,
Se-,
and
S-amide
moieties
are
present
in
many
medicinally
active
molecules,
but
their
synthesis
remains
challenging.
Here,
we
demonstrate
a
high-throughput
using
amide-sulfoxonium
ylides
as
carbene
precursors
Si-H,
Ge-H,
B-H,
Se-H,
S-H
insertion
reactions
to
target
wide
range
of
α-silyl,
α-geryl,
α-boryl,
α-selenyl,
α-sulfur
(hetero)amides.
The
process
is
featured
simple
operation,
mild
conditions,
broad
substrate
scope,
high
functional
group
compatibility,
excellent
chemoselectivity.
Both
experimental
computational
studies
conducted
explore
the
mechanisms
underlying
formation
C-Si/Ge/B/Se/S
bond.
This
research
highlights
use
highly
selective
X-H
with
ylide-derived
carbenes,
paving
way
for
preparation
diverse
organosilane,
organogermane,
organoboron,
organoselenium,
organosulfur
compounds
from
accessible
bench-stable
precursors.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(16), P. 2872 - 2882
Published: July 7, 2022
Abstract
A
metal‐free,
base‐mediated
decyanation
of
α‐aminonitriles
has
been
developed
to
synthesize
secondary
and
tertiary
amides
using
O
2
or
air
as
an
amide
oxygen
source.
Radical
scavenging
studies
disclosed
that
the
cleavage
C−CN
bond
may
proceed
via
anionic
pathway.
The
practicality
work
was
also
demonstrated
through
in
situ
generated
from
corresponding
aldehydes
amines
afford
amides.
important
features
this
include
broad
functional
group
compatibility,
41%
89%
product
yields,
gram‐scale
synthesis
2°
3°
amides,
substrate
scope,
umpolung
strategy.
magnified
image
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(17), P. 11545 - 11556
Published: Aug. 16, 2021
α,β-Unsaturated
carbonyl
compounds
are
significant
moieties
in
many
biological
molecules
and
have
attracted
considerable
attention
organic
synthetic
chemistry.
A
Pd-catalyzed
cascade
cyclization
for
the
synthesis
of
(E)-α,β-unsaturated
with
sequential
formation
C–C
bonds
was
developed.
This
method
offers
high
efficiency,
good
functional
group
tolerance,
moderate
to
excellent
yields
generally
displays
stereoselectivity.
New Journal of Chemistry,
Journal Year:
2022,
Volume and Issue:
46(21), P. 9994 - 9998
Published: Jan. 1, 2022
A
simple
and
novel
metal-free
reduction
of
azides
to
amines
in
the
presence
DBU
is
reported.
This
DBU-promoted
transformation
features
good
functional
group
tolerance
high
chemo-selectivity.
