European Journal of Organic Chemistry,
Год журнала:
2018,
Номер
2018(44), С. 6050 - 6067
Опубликована: Июль 11, 2018
Amino
acids
and
peptides
play
an
important
role
in
nature,
as
well
organic
pharmaceutical
chemistry.
Therefore,
the
easy,
straightforward
versatile
access
of
biogenic
unnatural
derivatives
is
still
highly
demanding.
This
micro‐review
intends
to
provide
reader
current
state
art
on
site‐selective
C–H
bond
functionalization
technology
applied
α‐amino
peptides,
focusing
different
positions
that
can
successfully
be
addressed
date.
It
structured
two
main
parts
implying
i)
α‐C–H
at
peptide
backbone
ii)
modification
side‐chain.
Herein,
metal‐catalyzed
activation,
oxidative
functionalization,
light
mediated
approaches,
are
discussed
considering
challenges
reactivity
selectivity.
The
great
potential
these
transformations
also
depicted
with
derivatization
macrocyclization
complex
leading
products
importance.
Chemical Society Reviews,
Год журнала:
2018,
Номер
47(17), С. 6603 - 6743
Опубликована: Янв. 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,
Год журнала:
2020,
Номер
120(3), С. 1788 - 1887
Опубликована: Янв. 6, 2020
During
the
past
decades,
synthetic
organic
chemistry
discovered
that
directing
group
assisted
C–H
activation
is
a
key
tool
for
expedient
and
siteselective
construction
of
C–C
bonds.
Among
various
strategies,
bidentate
groups
are
now
recognized
as
one
most
efficient
devices
selective
functionalization
certain
positions
due
to
fact
its
metal
center
permits
fine,
tunable,
reversible
coordination.
The
family
permit
types
assistance
be
achieved,
such
N,N-dentate,
N,O-dentate,
N,S-dentate
auxiliaries,
which
categorized
based
on
coordination
site.
In
this
review,
we
broadly
discuss
bond
reactions
formation
bonds
with
aid
groups.
Chemical Reviews,
Год журнала:
2020,
Номер
120(5), С. 2613 - 2692
Опубликована: Фев. 17, 2020
Transition-metal
catalyzed
reactions
that
are
able
to
construct
complex
aliphatic
amines
from
simple,
readily
available
feedstocks
have
become
a
cornerstone
of
modern
synthetic
organic
chemistry.
In
light
the
ever-increasing
importance
across
range
chemical
sciences,
this
review
aims
provide
concise
overview
transition-metal
approaches
alkylamine
synthesis
and
their
functionalization.
Selected
examples
amine
bond
forming
include:
(a)
hydroamination
hydroaminoalkylation,
(b)
C(sp3)–H
functionalization,
(c)
visible-light-mediated
photoredox
catalysis.
Angewandte Chemie International Edition,
Год журнала:
2017,
Номер
57(1), С. 62 - 101
Опубликована: Дек. 5, 2017
Abstract
The
functionalization
of
C(sp
3
)−H
bonds
streamlines
chemical
synthesis
by
allowing
the
use
simple
molecules
and
providing
novel
synthetic
disconnections.
Intensive
recent
efforts
in
development
new
reactions
based
on
C−H
have
led
to
its
wider
adoption
across
a
range
research
areas.
This
Review
discusses
strengths
weaknesses
three
main
approaches:
transition‐metal‐catalyzed
activation,
1,
n
‐hydrogen
atom
transfer,
carbene/nitrene
for
directed
unactivated
bonds.
For
each
strategy,
scope,
reactivity
different
bonds,
position
reacting
relative
directing
group,
stereochemical
outcomes
are
illustrated
with
examples
literature.
aim
this
is
provide
guidance
inspire
future
area.
Chemical Reviews,
Год журнала:
2021,
Номер
122(6), С. 5682 - 5841
Опубликована: Окт. 18, 2021
Transition-metal-catalyzed
C–H
activation
has
developed
a
contemporary
approach
to
the
omnipresent
area
of
retrosynthetic
disconnection.
Scientific
researchers
have
been
tempted
take
help
this
methodology
plan
their
synthetic
discourses.
This
paradigm
shift
helped
in
development
industrial
units
as
well,
making
synthesis
natural
products
and
pharmaceutical
drugs
step-economical.
In
vast
zone
bond
activation,
functionalization
proximal
bonds
gained
utmost
popularity.
Unlike
bonds,
distal
is
more
strenuous
requires
distinctly
specialized
techniques.
review,
we
compiled
various
methods
adopted
functionalize
mechanistic
insights
within
each
these
procedures,
scope
methodology.
With
give
complete
overview
expeditious
progress
made
field
organic
chemistry
while
also
highlighting
its
pitfalls,
thus
leaving
open
for
further
modifications.
Chemical Reviews,
Год журнала:
2022,
Номер
122(15), С. 12544 - 12747
Опубликована: Июль 17, 2022
1,1,1,3,3,3-Hexafluoroisopropanol
(HFIP)
is
a
polar,
strongly
hydrogen
bond-donating
solvent
that
has
found
numerous
uses
in
organic
synthesis
due
to
its
ability
stabilize
ionic
species,
transfer
protons,
and
engage
range
of
other
intermolecular
interactions.
The
use
this
exponentially
increased
the
past
decade
become
choice
some
areas,
such
as
C–H
functionalization
chemistry.
In
review,
following
brief
history
HFIP
an
overview
physical
properties,
literature
examples
reactions
using
or
additive
are
presented,
emphasizing
effect
each
reaction.
Angewandte Chemie International Edition,
Год журнала:
2018,
Номер
57(45), С. 14700 - 14717
Опубликована: Июль 3, 2018
The
late-stage
modification
of
structurally
complex
peptides
bears
great
potential
for
drug
discovery,
crop
protection,
and
the
pharmaceutical
industry,
among
others.
Whereas
traditional
approaches
largely
rely
on
prefunctionalizations,
C-H
activation
catalysis
has
in
recent
years
emerged
as
an
increasingly
powerful
tool
post-translational
peptide
modifications
a
step-economic
manner.
Herein,
we
summarize
progress
organometallic
until
June
2018,
including
position-
chemoselective
palladium-,
ruthenium-,
manganese-catalyzed
processes.
Journal of the American Chemical Society,
Год журнала:
2016,
Номер
138(44), С. 14554 - 14557
Опубликована: Окт. 27, 2016
Pd(II)-catalyzed
γ-C(sp3)–H
arylation
of
primary
amines
is
realized
by
using
2-hydroxynicotinaldehyde
as
a
catalytic
transient
directing
group.
Importantly,
the
catalyst
and
group
loading
can
be
lowered
to
2%
4%
respectively,
thus
demonstrating
high
efficiency
this
newly
designed
Heterocyclic
aryl
iodides
are
also
compatible
with
reaction.
Furthermore,
swift
synthesis
1,2,3,4-tetrahydronaphthyridine
derivatives
accomplished
Journal of the American Chemical Society,
Год журнала:
2017,
Номер
139(38), С. 13579 - 13584
Опубликована: Сен. 1, 2017
A
direct
hydroalkylation
of
disubstituted
alkynes
with
unfunctionalized
ethers
and
amides
was
achieved
in
an
atom-efficient
additive-free
manner
through
the
synergistic
combination
photoredox
nickel
catalysis.
The
protocol
effective
a
wide
range
internal
alkynes,
providing
products
highly
selective
fashion.
Notably,
observed
regioselectivity
is
complementary
to
conventional
radical
addition
processes.
Mechanistic
investigations
suggest
that
photoexcited
iridium
catalyst
facilitated
activation
via
single-electron
transfer.