Comptes Rendus Chimie,
Год журнала:
2024,
Номер
27(G1), С. 353 - 383
Опубликована: Дек. 3, 2024
The
development
of
chiral
fluorinated
biomolecules
such
as
amino
acids,
peptides
and
pseudopeptides
is
attracting
considerable
interest
at
the
frontiers
organic
synthesis
biological
chemistry.
We
propose
in
this
review
an
overview
our
contributions
to
organofluorine
chemistry
connection
with
applications
also
asymmetric
these
past
twenty
years
Université
de
Cergy-Pontoise
(now
CY
Cergy
Paris
Université).
Le
développement
biomolécules
fluorées
chirales
telles
que
les
acides
aminés,
et
suscite
un
intérêt
considérable
aux
frontières
la
synthèse
organique
chimie
biologique.
Nous
proposons
dans
cette
revue
aperçu
nos
le
domaine
des
composés
organofluorés
pour
biologiques
mais
aussi
asymétrique
ces
vingt
dernières
années
à
l'Université
(maintenant
Organic Letters,
Год журнала:
2024,
Номер
26(19), С. 4065 - 4070
Опубликована: Май 2, 2024
We
introduce
a
novel
and
straightforward
methodology
for
photoredox
arylation
of
an
indole
scaffold
using
aryldiazonium
salts
under
mild
metal-free
conditions.
Our
approach
enables
the
regioselective
chemoselective
introduction
several
aryl
groups
to
C(2)
position
indoles
tryptophan,
even
in
competition
with
other
amino
acids.
This
extends
late-stage
functionalization
peptides
lysozyme,
heralding
unprecedented
tryptophan
residues
wild-type
proteins
offering
broad
utility
chemical
biology.
As
the
least
abundant
residue
in
proteins,
tryptophan
widely
exists
peptide
drugs
and
bioactive
natural
products
contributes
to
drug-target
interactions
multiple
ways.
We
report
here
a
clickable
modification
for
late-stage
diversification
of
native
peptides,
via
catalyst-free
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(17), С. 11950 - 11958
Опубликована: Авг. 19, 2024
An
environmentally
friendly
electrochemical
strategy
for
the
synthesis
of
SCF3-containing
oxindoles
was
developed.
This
transformation
accomplished
through
a
cascade
trifluoromethylthiolation/cyclization
N-acrylamides
with
AgSCF3,
obviating
requirement
external
oxidants.
A
variety
functional
groups
were
well
tolerated
in
this
transformation.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(16), С. 11588 - 11592
Опубликована: Авг. 4, 2024
This
work
reports
a
method
for
the
catalytic
synthesis
of
C(3)
SCF3-substituted
pyrrolidinindoline
using
small-ring
organophosphorus-based
catalyst
and
hydrosilane
reductant,
with
trifluoromethanesulfonyl
chloride
as
electrophilic
SCF3
reagent.
can
drive
conversion
tryptamine
to
pyrrolidine
indoline.
The
readily
available,
inexpensive
could
be
activated
an
source
by
PIII/PV
redox
catalysis
efficiently
participate
in
reaction
tryptamines,
thus
providing
various
substituted
pyrrolidinoindoline
moderate
excellent
yields.
presented
strategy
features
broad
substrate
scope,
structure
has
value
in-depth
research.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
89(2), С. 1275 - 1284
Опубликована: Дек. 29, 2023
Incorporation
of
the
highly
lipophilic
trifluoromethanesulfenyl
group
into
bioactive
molecules
facilitates
transport
through
lipid
membranes,
and
thus,
CF
The Journal of Physical Chemistry Letters,
Год журнала:
2024,
Номер
15(25), С. 6611 - 6620
Опубликована: Июнь 18, 2024
Amphiphilic
peptides
show
great
potential
for
exfoliating
graphite
and
functionalizing
graphene.
However,
the
variety
of
amino
acids
complicates
our
understanding
underlying
mechanisms.
In
this
study,
we
designed
four
(C6W1,
C6W2,
C6W4,
C6W6)
with
different
amounts
aromatic
tryptophan
two
additional
(C6F4
C6Y4)
by
substituting
phenylalanine
or
tyrosine.
This
allowed
us
to
investigate
processes
mechanisms
exfoliation
graphene
functionalization.
Using
experimental
computational
methods,
discovered
that
containing
demonstrated
higher
efficiency
increased
content
further
improved
efficiency,
resulting
in
more
peptide-functionalized
layers.
Significantly,
primary
driving
force
surface-assisted
assembly
on
is
π–π
stacking
interaction
between
ring
contributed
hexagonal
rings
surface.
leads
a
layer-by-layer
mechanism.
Our
research
offers
valuable
insights
into
peptide
design
strategies
one-step
functionalization
aqueous
environments.
We
report
herein
an
efficient
and
site-selective
electrophilic
trifluoromethylthiolation
of
indolines.
In
the
absence
any
catalyst
or
additive,
C5-selective
could
proceed
at
room
temperature.
With
palladium
used
as
catalyst,
selectivity
was
reversed
completely,
giving
C7-selecive
trifluoromethylthiolated
products.
This
reaction
features
good
functional
group
tolerance,
simple
operation,
mild
conditions,
scale-up
application.
The
potential
utilities
products
were
shown
by
further
transformations.
