Journal of the American Chemical Society,
Journal Year:
2017,
Volume and Issue:
139(41), P. 14511 - 14517
Published: Aug. 6, 2017
Carboranyl
aldehydes
are
among
the
most
useful
synthons
in
derivatization
of
carboranes.
However,
compared
to
utilization
carboranyl
carboxylic
acids
selective
B–H
bond
functionalizations,
synthetic
application
is
limited
due
weakly
coordinating
nature
aldehyde
group.
Herein,
direct
arylation
o-carboranyl
has
been
developed
via
Pd-catalyzed
cage
functionalization.
With
help
glycine
generate
a
directing
group
(DG)
situ,
series
B(4,5)-diarylated-
and
B(4)-monoarylated-o-carboranyl
were
obtained
good
excellent
yields
with
high
selectivity.
A
wide
range
functional
groups
tolerated.
The
arylated
products
could
be
readily
removed
or
transformed
into
methanol.
plausible
catalytic
cycle
for
was
proposed
based
on
control
experiments
stoichiometric
reactions,
including
isolation
key
bicyclic
palladium
complex.
Chemical Society Reviews,
Journal Year:
2018,
Volume and Issue:
47(17), P. 6603 - 6743
Published: Jan. 1, 2018
The
present
review
is
devoted
to
summarizing
the
recent
advances
(2015-2017)
in
field
of
metal-catalysed
group-directed
C-H
functionalisation.
In
order
clearly
showcase
molecular
diversity
that
can
now
be
accessed
by
means
directed
functionalisation,
whole
organized
following
directing
groups
installed
on
a
substrate.
Its
aim
comprehensive
reference
work,
where
specific
group
easily
found,
together
with
transformations
which
have
been
carried
out
it.
Hence,
primary
format
this
schemes
accompanied
concise
explanatory
text,
are
ordered
sections
according
their
chemical
structure.
feature
typical
substrates
used,
products
obtained
as
well
required
reaction
conditions.
Importantly,
each
example
commented
respect
most
important
positive
features
and
drawbacks,
aspects
such
selectivity,
substrate
scope,
conditions,
removal,
greenness.
targeted
readership
both
experts
functionalisation
chemistry
(to
provide
overview
progress
made
last
years)
and,
even
more
so,
all
organic
chemists
who
want
introduce
way
thinking
for
design
straightforward,
efficient
step-economic
synthetic
routes
towards
molecules
interest
them.
Accordingly,
should
particular
also
scientists
from
industrial
R&D
sector.
overall
goal
promote
application
reactions
outside
research
dedicated
method
development
establishing
it
valuable
archetype
contemporary
R&D,
comparable
role
cross-coupling
play
date.
Chemical Reviews,
Journal Year:
2021,
Volume and Issue:
121(21), P. 13051 - 13085
Published: Aug. 11, 2021
Merging
hydrogen
(H2)
evolution
with
oxidative
organic
synthesis
in
a
semiconductor-mediated
photoredox
reaction
is
extremely
attractive
because
the
clean
H2
fuel
and
high-value
chemicals
can
be
coproduced
under
mild
conditions
using
light
as
sole
energy
input.
Following
this
dual-functional
photocatalytic
strategy,
dreamlike
pathway
for
constructing
C–C/C–X
(X
=
C,
N,
O,
S)
bonds
from
abundant
readily
available
X–H
bond-containing
compounds
concomitant
release
of
fulfilled
without
need
external
chemical
reagents,
thus
offering
green
fascinating
synthetic
strategy.
In
review,
we
begin
by
presenting
concise
overview
on
general
background
traditional
production
then
focus
fundamental
principles
cooperative
coupling
selective
simultaneous
utilization
photoexcited
electrons
holes
over
semiconductor-based
catalysts
to
meet
economic
sustainability
goal.
Thereafter,
put
dedicated
emphasis
recent
key
progress
various
transformations,
including
alcohol
oxidation,
methane
conversion,
amines
coupling,
cross-coupling,
cyclic
alkanes
dehydrogenation,
reforming
lignocellulosic
biomass,
so
on.
Finally,
remaining
challenges
future
perspectives
flourishing
area
have
been
critically
discussed.
It
anticipated
that
review
will
provide
enlightening
guidance
rational
design
such
system,
thereby
stimulating
development
economical
environmentally
benign
solar
generation
value-added
fine
chemicals.
Accounts of Chemical Research,
Journal Year:
2018,
Volume and Issue:
51(2), P. 534 - 547
Published: Feb. 8, 2018
ConspectusAxially
chiral
compounds
have
received
much
attention
from
chemists
because
of
their
widespread
appearance
in
natural
products,
biologically
active
compounds,
and
useful
ligands
asymmetric
catalysis.
Because
the
importance
this
structural
motif,
catalytic
enantioselective
construction
axially
scaffolds
has
been
intensively
investigated,
great
progress
accomplished.
However,
majority
methodologies
field
focus
on
use
metal
catalysis,
whereas
approaches
involving
organocatalysis
started
to
emerge
only
recently.
This
Account
describes
certain
advances
organocatalytic
synthesis
following
strategies:
kinetic
resolution,
desymmetrization,
cyclization/addition,
direct
arylation,
so
on.
We
began
our
investigation
by
developing
a
highly
efficient
strategy
for
resolution
BINAM
derivatives
Brønsted
acid-catalyzed
imine
formation
transfer
hydrogenation
cascade
process,
thereby
providing
convenient
route
generate
high
yields
with
excellent
enantioselectivities.
The
desymmetrization
1-aryltriazodiones
(ATADs)
through
an
organocatalyzed
tyrosine
clicklike
reaction
wherein
nucleophile
was
added
ATAD
afforded
interesting
type
N-arylurazole
remote
enantiocontrolled
manner.
then
focused
cyclization
addition
given
inherent
limitations
terms
chemical
yield
substrate
scope.
By
utilizing
Paal–Knorr
reaction,
we
disclosed
general
method
access
enantiomerically
pure
arylpyrroles.
heterocycle
stepwise
method,
which
executed
one-pot
fashion
containing
subsequent
aromatization,
were
successfully
applied
diverse
arylquinazolinones
catalyzed
acids.
discovered
approach
construct
styrenes
1,4-addition
arylalkynals
good
Such
motifs
are
important
precursors
further
transformations
into
synthetic
intermediates
may
potential
applications
syntheses
as
olefin
or
organocatalysts.
To
tackle
challenge,
accomplished
phosphoric
arylative
reactions
2-naphthol
2-naphthamine
quinone
deliver
class
BINOL
NOBIN
enantioselectivities
under
mild
conditions.
Most
importantly,
that
azo
group
can
effectively
perform
directing
activating
formal
aryl
C–H
functionalization
via
nucleophilic
aromatic
substitution
azobenzene
derivatives.
Thus,
wide
range
arylindoles
synthesized
anticipate
will
foster
development
many
other
motivate
new
enthusiasm
functionalization.
Moreover,
SPINOLs
fundamental
organocatalysts
ligands.
developed
SPINOLs.
is
convergent
functional-group-tolerant
generation
results,
thus
delivering
practical
privileged
structure.
Chemical Reviews,
Journal Year:
2019,
Volume and Issue:
119(12), P. 6769 - 6787
Published: May 10, 2019
Photo-/electrochemical
catalyzed
oxidative
R1-H/R2-H
cross-coupling
with
hydrogen
evolution
has
become
an
increasingly
important
issue
for
molecular
synthesis.
The
dream
of
construction
C-C/C-X
bonds
from
readily
available
C-H/X-H
release
H2
can
be
facilely
achieved
without
external
chemical
oxidants,
providing
a
greener
model
bond
formation.
Given
the
great
influence
these
reactions
in
organic
chemistry,
we
give
summary
state
art
via
photo/electrochemistry,
and
hope
this
review
will
stimulate
development
synthetic
strategy
near
future.
Chemical Reviews,
Journal Year:
2021,
Volume and Issue:
121(24), P. 14957 - 15074
Published: Oct. 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.
Angewandte Chemie International Edition,
Journal Year:
2017,
Volume and Issue:
57(3), P. 744 - 748
Published: Nov. 8, 2017
Abstract
A
photoinduced
cascade
strategy
leading
to
a
variety
of
differentially
functionalised
nitriles
and
ketones
has
been
developed.
These
reactions
rely
on
the
oxidative
generation
iminyl
radicals
from
simple
oximes.
Radical
transposition
by
C(sp
3
)−(sp
)
)−H
bond
cleavage
gives
access
distal
carbon
that
undergo
S
H
2
functionalisations.
mild,
visible‐light‐mediated
procedures
can
be
used
for
remote
fluorination,
chlorination,
azidation,
were
applied
modification
bioactive
structurally
complex
molecules.
Macromolecules,
Journal Year:
2017,
Volume and Issue:
50(18), P. 6979 - 6997
Published: Sept. 17, 2017
The
ideal
of
living
polymerization
has
defined
research
in
polymer
chemistry
over
the
past
50
years.
In
this
Perspective,
we
present
case
that
concept
enabled
treatment
polymers
as
organic
molecules,
rather
than
impure
mixtures
species,
and
allowed
translation
methods
developed
by
synthetic
chemists
into
ever
more
accessible
and/or
controlled
methods.
concurrent
development
rapid
analytical
for
screening
new
characteristics,
chiefly
size
exclusion
chromatography,
greatly
aided
expansion
Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
59(45), P. 19773 - 19786
Published: July 20, 2020
Abstract
Transition
metal‐catalyzed
enantioselective
functionalization
of
C−H
bond,
the
most
abundant
functionality
in
organic
molecules,
has
emerged
as
an
expedient
synthetic
approach
to
streamline
synthesis
complex
chiral
molecules.
Despite
significant
progress,
traditional
directing
group‐enabled
strategies
require
additional
steps
for
installation
and
removal
groups
from
target
molecule.
The
recently
developed
asymmetric
using
transient
(
c
TDGs)
offers
a
promising
alternative
that
can
circumvent
this
obstacle
therefore
simplify
process.
In
Minireview,
we
briefly
discuss
advent
recent
advances
emerging
concept,
with
emphasis
on
discussing
creation
various
stereogenic
centers
developments
TDGs.
Applications
natural
product
ligand
derivatizations
are
also
discussed.
We
hope
Minireview
will
highlight
great
potential
strategy
help
inspire
further
endeavors.