Abstract
The
difluoromethyl
group
(CF2H)
can
function
as
a
lipophilic
hydrogen-bond
donor,
and
is
regarded
bioisostere
of
functional
groups
such
hydroxy
(-OH),
thiol
(-SH),
amino
(-NH2).
unique
physicochemical
properties
this
make
difluoromethylation
hot
topic
in
the
field
synthetic
organic
chemistry,
recent
decades,
various
methods
have
been
developed
for
constructing
C(sp3)—CF2H,
C(sp2)—CF2H,
C(sp)
—CF2H,
X—CF2H
(X
=
N,
O,
S,
Se,
B,
P,
etc.)
bonds.
This
review
summarizes
currently
available
reagents
performing
reactions,
well
other
approaches
installing
unit.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(24), С. 17134 - 17143
Опубликована: Дек. 6, 2023
It
is
significant
to
develop
novel
difluoromethylation
methods
because
of
the
important
roles
difluoromethyl
groups
in
medicinal
chemistry
and
material
industries.
Here,
we
developed
a
difluoromethylation–carboxylation
difluoromethylation–deuteration
method
triggered
by
radical
generated
electroreduction
stable
easily
available
difluoromethyltriphenylphosphonium
bromide.
Various
molecules
containing
carboxyl
or
deuterium
can
be
synthesized
through
this
method.
The
establishment
will
provide
an
alternative
reactions.
Angewandte Chemie,
Год журнала:
2024,
Номер
136(34)
Опубликована: Июнь 4, 2024
Abstract
Recently,
the
introduction
of
fluorosulfonyl
(−SO
2
F)
groups
have
attracted
considerable
research
interests,
as
this
moiety
could
often
afford
enhanced
activities
and
new
functions
in
context
chemical
biology
drug
discovery.
Herein,
we
report
design
synthesis
1‐fluorosulfamoyl‐pyridinium
(FSAP)
salts,
which
serve
an
effective
photoredox‐active
precursor
to
fluorosulfamoyl
radicals
enable
direct
radical
C−H
fluorosulfonamidation
a
variety
(hetero)arenes.
This
method
features
mild
conditions,
visible
light,
broad
substrate
scope,
good
group
tolerance,
etc.,
metal‐free
protocol
is
also
viable
by
using
organic
photocatalysts.
Further,
FSAP
can
be
applied
functionalization
alkenes
via
1,2‐difunctionalization,
distal
migration,
tandem
radical‐polar
crossover
reactions,
etc.
In
addition,
formal
methylamination
(hetero)arenes
combining
with
subsequent
hydrolysis
well
product
derivatization
are
demonstrated.
Patai's chemistry of functional groups,
Год журнала:
2024,
Номер
unknown, С. 1 - 75
Опубликована: Дек. 23, 2024
Abstract
Difluoromethyl
compounds
have
found
increasingly
important
applications
in
the
fields
of
pharmaceuticals
and
agrochemicals
due
to
unique
biological
properties
CF
2
H
group.
The
past
decade
has
witnessed
development
an
impressive
array
new
reagents
strategies
for
efficient
difluoromethylation.
This
review
aims
summarize
state‐of‐the‐art
advances
difluoromethylation
according
following
four
categories:
electrophilic
difluoromethylation,
nucleophilic
radical
transition‐metal
mediated
Abstract
The
difluoromethyl
group
(CF2H)
can
function
as
a
lipophilic
hydrogen-bond
donor,
and
is
regarded
bioisostere
of
functional
groups
such
hydroxy
(-OH),
thiol
(-SH),
amino
(-NH2).
unique
physicochemical
properties
this
make
difluoromethylation
hot
topic
in
the
field
synthetic
organic
chemistry,
recent
decades,
various
methods
have
been
developed
for
constructing
C(sp3)—CF2H,
C(sp2)—CF2H,
C(sp)
—CF2H,
X—CF2H
(X
=
N,
O,
S,
Se,
B,
P,
etc.)
bonds.
This
review
summarizes
currently
available
reagents
performing
reactions,
well
other
approaches
installing
unit.
