Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(11), P. 4143 - 4147
Published: May 24, 2019
The
efficient
couplings
of
diverse
N-arylureas
and
methyleneoxetanones
have
been
realized
via
Rh(III)-catalyzed
solvent-controlled
chemoselective
C–H
functionalization,
which
involved
the
tunable
β-H
elimination
β-O
processes,
thereby
giving
divergent
access
to
quinolin-2(1H)-ones
ortho-allylated
with
broad
substrate
compatibility
good
functional
group
tolerance.
synthetic
utilities
transformations
also
exemplified
by
subsequently
tandem
allylation,
unsymmetrical
alternative
reaction
mode,
as
well
removal
carbamoyl
group.
ACS Catalysis,
Journal Year:
2021,
Volume and Issue:
11(22), P. 13921 - 13934
Published: Nov. 2, 2021
Exploring
multistep
cascade
reactions
triggered
by
C–H
activation
are
recognized
as
appealing,
yet
challenging.
Herein,
we
disclose
a
Rh(III)-catalyzed
domino
coupling
of
N-carbamoyl
indoles
and
4-hydroxy-2-alkynoates
for
the
streamlined
assembly
highly
functionalized
furan-2(5H)-ones
in
which
carbamoyl-directing
group
(DG)
is
given
dual
role
an
auxiliary
migrating
acylating
reagent
via
cleavage
stable
C–N
bonds
at
room
temperature.
More
importantly,
obtained
furan-2(5H)-one
skeleton
could
be
further
under
air
situ
C5–H
hydroxylation
simply
switching
solvent
or
additive,
providing
fully
substituted
with
installation
alcohol-based
C5
quaternary
carbon
center.
Detailed
experimental
studies
density
functional
theory
calculations
reveal
that
Rh(III)-mediated
tandem
activation/alkyne
insertion/DG
migration/lactonization
accounts
developed
transformation
to
achieve
high
functionalities
observed
exclusive
selectivity.
The
potential
biological
application
class
potent
PPARγ
ligands
highlights
synthetic
utility
methodology.
This
protocol
endowed
several
salient
features
including
efficient
activation,
excellent
chemo-,
regio-,
stereoselectivity,
bond-forming
efficiency
(e.g.,
two
C–C
C–O
bonds),
solvent-
additive-controlled
product
selectivity,
good
functional-group
compatibility,
mild
redox-neutral
conditions.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(15), P. 5952 - 5957
Published: July 29, 2021
The
Rh(III)-catalyzed
dual
directing
group
assisted
C–H
activation/annulation
of
3-arylisoxazolones
with
propargyl
alcohols
has
been
developed,
which
expands
the
application
scope
isoxazolones
in
organic
synthesis.
This
protocol
also
worked
well
3-aryl-1,4,2-dioxazol-5-ones
to
produce
synthetically
and
biologically
important
4-arylisoquinolones.
Green Chemistry,
Journal Year:
2022,
Volume and Issue:
24(18), P. 7012 - 7021
Published: Jan. 1, 2022
A
robust
and
convenient
rhodium-catalyzed
unconventionally
regioselective
C–H
activation/[4
+
2]
annulation
for
the
synthesis
of
isoquinolones
which
are
prevalent
in
natural
products
pharmaceuticals
was
developed.
Organic Letters,
Journal Year:
2018,
Volume and Issue:
20(21), P. 6812 - 6816
Published: Oct. 24, 2018
A
unique
Rh(III)-catalyzed
oxidative
[5
+
2]
annulation
of
easily
available
2-alkenylphenols
with
propargyl
carbonates
have
been
developed
by
using
two
O-containing
functional
groups
as
the
traceless
assisting
(AGs).
The
experimental
investigations
together
density
theory
(DFT)
calculations
revealed
that
this
transformation
involves
free
OH-directed
cleavage
one
terminal
C–H
bond
alkenyl
moiety
and
regioselective
alkyne
insertion,
followed
OBoc-promoted
intramolecular
nucleophilic
substitution
β-H
elimination
used
an
allyl
species
active
intermediate,
giving
direct
access
to
3-alkenylated
benzoxepine
skeleton
broad
substrate
compatibility
good
group
tolerance.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(11), P. 4143 - 4147
Published: May 24, 2019
The
efficient
couplings
of
diverse
N-arylureas
and
methyleneoxetanones
have
been
realized
via
Rh(III)-catalyzed
solvent-controlled
chemoselective
C–H
functionalization,
which
involved
the
tunable
β-H
elimination
β-O
processes,
thereby
giving
divergent
access
to
quinolin-2(1H)-ones
ortho-allylated
with
broad
substrate
compatibility
good
functional
group
tolerance.
synthetic
utilities
transformations
also
exemplified
by
subsequently
tandem
allylation,
unsymmetrical
alternative
reaction
mode,
as
well
removal
carbamoyl
group.
