Organic Letters,
Год журнала:
2023,
Номер
25(24), С. 4422 - 4428
Опубликована: Июнь 8, 2023
Presented
herein
is
a
condition-controlled
selective
synthesis
of
pyranone-tethered
indazoles
or
carbazole
derivatives
via
the
cascade
reactions
N-nitrosoanilines
with
iodonium
ylides.
Mechanistically,
formation
former
involves
an
unprecedented
process
including
nitroso
group-directed
C(sp2)–H
bond
alkylation
N-nitrosoaniline
ylide
followed
by
intramolecular
C-nucleophilic
addition
to
moiety,
solvent-assisted
cyclohexanedione
ring
opening,
and
transesterification/annulation.
On
contrary,
latter
initial
annulation
denitrosation.
These
developed
protocols
feature
easily
controllable
selectivity,
mild
reaction
conditions,
clean
sustainable
oxidant
(air),
valuable
products
that
are
structurally
diverse.
In
addition,
utility
was
showcased
their
facile
diverse
transformations
into
synthetically
biologically
interesting
compounds.
Chemical Reviews,
Год журнала:
2021,
Номер
122(2), С. 1875 - 1924
Опубликована: Авг. 6, 2021
Direct
photocatalyzed
hydrogen
atom
transfer
(d-HAT)
can
be
considered
a
method
of
choice
for
the
elaboration
aliphatic
C–H
bonds.
In
this
manifold,
photocatalyst
(PCHAT)
exploits
energy
photon
to
trigger
homolytic
cleavage
such
bonds
in
organic
compounds.
Selective
bond
may
achieved
by
judicious
abstractor
(key
parameters
are
electronic
character
and
molecular
structure),
as
well
reaction
additives.
Different
classes
PCsHAT
available,
including
aromatic
ketones,
xanthene
dyes
(Eosin
Y),
polyoxometalates,
uranyl
salts,
metal-oxo
porphyrin
tris(amino)cyclopropenium
radical
dication.
The
processes
(mainly
C–C
formation)
most
cases
carried
out
under
mild
conditions
with
help
visible
light.
aim
review
is
offer
comprehensive
survey
synthetic
applications
d-HAT.
Chemical Reviews,
Год журнала:
2021,
Номер
121(24), С. 14957 - 15074
Опубликована: Окт. 29, 2021
Transition-metal-catalyzed,
coordination-assisted
C(sp3)–H
functionalization
has
revolutionized
synthetic
planning
over
the
past
few
decades
as
use
of
these
directing
groups
allowed
for
increased
access
to
many
strategic
positions
in
organic
molecules.
Nonetheless,
several
challenges
remain
preeminent,
such
requirement
high
temperatures,
difficulty
removing
or
converting
groups,
and,
although
metals
provide
some
reactivity,
employing
outside
palladium.
This
review
aims
give
a
comprehensive
overview
coordination-assisted,
transition-metal-catalyzed,
direct
nonactivated
bonds
by
covering
literature
since
2004
order
demonstrate
current
state-of-the-art
methods
well
limitations.
For
clarity,
this
been
divided
into
nine
sections
transition
metal
catalyst
with
subdivisions
type
bond
formation.
Synthetic
applications
and
reaction
mechanism
are
discussed
where
appropriate.
Chemical Reviews,
Год журнала:
2020,
Номер
120(13), С. 6124 - 6196
Опубликована: Июнь 3, 2020
A
critically
important
process
in
catalysis
is
the
formation
of
an
active
catalyst
from
combination
a
metal
precursor
and
ligand,
as
efficacy
this
reaction
governs
amount
catalyst.
This
Review
comprehensive
overview
reactions
catalyzed
by
nickel
added
bidentate
phosphine,
focusing
on
steps
transforming
precatalyst
ligand
into
potential
effects
transformation
catalysis.
Reactions
covered
include
common
cross-coupling
reactions,
such
Suzuki,
Heck,
Kumada,
Negishi
couplings,
addition
cycloadditions,
C–H
functionalizations,
polymerizations,
hydrogenations,
reductive
among
others.
Overall,
most
widely
used
with
free
phosphines
Ni(cod)2,
which
accounts
for
∼50%
reports
surveyed,
distantly
followed
Ni(acac)2
Ni(OAc)2,
account
∼10%
each.
By
compiling
these
we
have
calculated
statistics
usage
each
Ni(cod)2
other
sources.
The
are
simple,
relatively
inexpensive
ligands,
DPPE,
DCPE,
DPPP,
DPPB,
along
others
more
complex
backbones,
DPPF
Xantphos.
use
expensive
chiral
scattered,
but
ligands
BINAP,
Me-Duphos,
Josiphos,
related
analogs.
Organic Letters,
Год журнала:
2019,
Номер
21(6), С. 1895 - 1899
Опубликована: Март 6, 2019
Cp*Cobalt(III)-catalyzed
enantioselective
C-H
amidation
of
ferrocenes
using
monoprotected
amino
acids
(MPAAs)
as
chiral
ligands
was
developed.
The
reaction
performed
under
mild
conditions
in
high
yields
(up
to
97%)
with
moderate
enantioselectivity
77.5:22.5
er),
providing
a
promising
strategy
create
planar
chirality
via
base-metal-catalyzed
activation.
Chemical Society Reviews,
Год журнала:
2020,
Номер
49(15), С. 5310 - 5358
Опубликована: Янв. 1, 2020
This
review
highlights
the
developments
in
iron
and
cobalt
catalyzed
C(sp3)–H
bond
functionalization
reactions
with
emphasis
on
their
applications
organic
synthesis,
i.e.
natural
products
pharmaceuticals
synthesis
and/or
modification.
Chemical Society Reviews,
Год журнала:
2021,
Номер
50(5), С. 3263 - 3314
Опубликована: Янв. 1, 2021
Olefinic
C-H
functionalization
represents
an
atom-
and
step
economic
approach
to
valuable
olefin
derivatives
from
simpler
ones,
but
controlling
the
selectivity
remains
a
challenge.
Remarkable
progress
has
been
made
in
site-selective
of
arenes
alkanes,
there
are
still
limited
examples
selective
olefins
presumably
due
lability
easy
decomposition
alkenyl
moiety.
Chelation-assisted
activation
efficient
protocol
for
site-
stereo-selective
construction
carbon-carbon
carbon-heteroatom
bonds.
This
review
highlights
recent
advances
vicinal-
geminal-group-directed
olefinic
functionalization,
including
alkenylation,
arylation,
alkynylation,
alkylation,
halogenation,
silylation,
cyanation
annulation
by
formation
exo-/endo-metallocycles.
In
particular,
is
covered
first
time,
as
well
distal-selective
under
palladium/norbornene
cooperative
catalysis,
which
provides
novel
disconnections
retrosynthetic
analysis
future
trend
green
chemistry.
