ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(15), P. 11532 - 11544
Published: July 19, 2024
Glycosyl
donor
activation
emerged
as
an
enabling
technology
for
anomeric
functionalization,
but
aimed
primarily
at
O-glycosylation.
In
contrast,
we
herein
disclose
mechanistically
distinct
electrochemical
glycosyl
bromide
activations
via
halogen-atom
transfer
and
C-glycosylation.
The
radical
addition
to
alkenes
led
C-alkyl
glycoside
synthesis
under
precious
metal-free
reaction
conditions
from
readily
available
bromides.
robustness
of
our
e-XAT
strategy
was
further
mirrored
by
C-aryl
C-acyl
glycosides
assembly
through
nickela-electrocatalysis.
Our
approach
provides
orthogonal
with
expedient
scope,
hence
representing
a
general
method
direct
C-glycosides
assembly.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(31), P. 5756 - 5761
Published: July 28, 2023
Herein
we
report
a
nickel-catalyzed
regioselective
cross-electrophile
ring
opening
reaction
of
sulfonyl-protected
aziridines
with
trifluoromethyl-substituted
alkenes
as
the
gem-difluoroallylating
agents,
providing
new
and
efficient
entry
to
prepare
gem-difluorobishomoallylic
sulfonamides.
Moreover,
scaffold
6-fluoro-1,2,3,4-tetrahydropyridine
can
be
constructed
starting
from
products
via
NaH-mediated
intramolecular
defluorinative
nucleophilic
vinylic
substitution.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(8), P. 6228 - 6235
Published: April 10, 2024
Chiral
nickel
complexes
promoted
enantioselective
reductive
alkenylation
of
a
range
conjugated
enones,
using
alkenyl
bromides,
triflates,
and
tosylates.
The
neutral
condition
was
compatible
with
sensitive
groups
azaheteroaryl
rings.
Importantly,
in
products
can
be
readily
converted
to
functionalized
alkyl
via
iron-catalyzed
hydrofunctionalization.
Some
examples
asymmetric
N-enoyl
pyrroles
indoles
were
also
included.
Nature Communications,
Journal Year:
2024,
Volume and Issue:
15(1)
Published: March 28, 2024
Abstract
Transition
metal-catalyzed
enantioconvergent
cross-coupling
of
an
alkyl
precursor
presents
a
promising
method
for
producing
enantioenriched
C(sp
3
)
molecules.
Because
alcohol
is
ubiquitous
and
abundant
family
feedstock
in
nature,
the
direct
reductive
coupling
aryl
halide
enables
efficient
access
to
valuable
compounds.
Although
several
strategies
have
been
developed
overcome
high
bond
dissociation
energy
C
−
O
bond,
asymmetric
pattern
remains
unknown.
In
this
report,
we
describe
realization
deoxygenative
unactivated
(β-hydroxy
ketone)
bromide
presence
NHC
activating
agent.
The
approach
can
accommodate
substituents
various
sizes
functional
groups,
its
synthetic
potency
demonstrated
through
gram
scale
reaction
derivatizations
into
other
compound
families.
Finally,
apply
our
convergent
synthesis
four
β-aryl
ketones
that
are
natural
products
or
bioactive
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(15), P. 11532 - 11544
Published: July 19, 2024
Glycosyl
donor
activation
emerged
as
an
enabling
technology
for
anomeric
functionalization,
but
aimed
primarily
at
O-glycosylation.
In
contrast,
we
herein
disclose
mechanistically
distinct
electrochemical
glycosyl
bromide
activations
via
halogen-atom
transfer
and
C-glycosylation.
The
radical
addition
to
alkenes
led
C-alkyl
glycoside
synthesis
under
precious
metal-free
reaction
conditions
from
readily
available
bromides.
robustness
of
our
e-XAT
strategy
was
further
mirrored
by
C-aryl
C-acyl
glycosides
assembly
through
nickela-electrocatalysis.
Our
approach
provides
orthogonal
with
expedient
scope,
hence
representing
a
general
method
direct
C-glycosides
assembly.
