Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 16, 2024
Comprehensive
Summary
Traditional
protecting
groups
are
often
removed
under
harsh
conditions
with
potentially
hazardous
reagents,
thereby
impeding
the
convenient
synthesis
of
oligosaccharides
and
glycosides.
Herein,
we
present
to
utilize
photolabile
ortho
‐nitro‐benzyl
carbonate
(
o
NBC)
as
a
permanent
hydroxyl
group
for
stereocontrolled
The
Ph
3
PO‐modulated
glycosylation
strongly
disarmed
per‐
O
‐
NBC‐protected
glycosyl
ynenoates
preferred
afford
glycosides
excellent
α‐selectivities
via
β‐phosphonium
transition
state.
Based
on
NBC‐mediated
galactosylation,
glycolipid
digalactosyl
diacylglycerol
(DGDG)
containing
six
double
bonds
two
esters
was
achieved
in
straightforward
manner.
Chemical Reviews,
Journal Year:
2021,
Volume and Issue:
122(2), P. 2752 - 2906
Published: Aug. 10, 2021
Photoinduced
chemical
transformations
have
received
in
recent
years
a
tremendous
amount
of
attention,
providing
plethora
opportunities
to
synthetic
organic
chemists.
However,
performing
photochemical
transformation
can
be
quite
challenge
because
various
issues
related
the
delivery
photons.
These
challenges
barred
widespread
adoption
steps
industry.
past
decade,
several
technological
innovations
led
more
reproducible,
selective,
and
scalable
photoinduced
reactions.
Herein,
we
provide
comprehensive
overview
these
exciting
advances,
including
flow
chemistry,
high-throughput
experimentation,
reactor
design
scale-up,
combination
photo-
electro-chemistry.
iScience,
Journal Year:
2021,
Volume and Issue:
24(3), P. 102209 - 102209
Published: Feb. 21, 2021
Visible
light
photocatalysis
has
become
a
powerful
tool
in
organic
synthesis
that
uses
photons
as
traceless,
sustainable
reagents.
Most
of
the
activities
field
focus
on
development
new
reactions
via
common
photoredox
cycles,
but
recently
number
exciting
concepts
and
strategies
entered
less
charted
territories.
We
survey
approaches
enable
use
longer
wavelengths
show
wavelength
intensity
are
import
parameters
tuning
reactivity
photocatalyst
to
control
or
change
selectivity
chemical
reactions.
In
addition,
we
discuss
recent
efforts
substitute
strong
reductants,
such
elemental
lithium
sodium,
by
technological
advances
field.
Chemical Society Reviews,
Journal Year:
2023,
Volume and Issue:
52(22), P. 7773 - 7801
Published: Jan. 1, 2023
The
structural
complexity
of
glycans
poses
a
serious
challenge
in
the
chemical
synthesis
glycosides,
oligosaccharides
and
glycoconjugates.
Glycan
complexity,
determined
by
composition,
connectivity,
configuration
far
exceeds
what
nature
achieves
with
nucleic
acids
proteins.
Consequently,
glycoside
ranks
among
most
complex
tasks
organic
synthesis,
despite
involving
only
simple
type
bond-forming
reaction.
Here,
we
introduce
fundamental
principles
bond
formation
summarize
recent
advances
oligosaccharide
synthesis.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(4), P. 1204 - 1236
Published: Jan. 1, 2024
This
review
article
highlights
the
diverse
ways
in
which
recent
developments
areas
of
photocatalysis
and
visible
light
photochemistry
are
impacting
synthetic
carbohydrate
chemistry.
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
60(13), P. 6965 - 6969
Published: Feb. 5, 2021
Abstract
Controlling
the
selectivity
of
a
chemical
reaction
with
external
stimuli
is
common
in
thermal
processes,
but
rare
visible‐light
photocatalysis.
Here
we
show
that
redox
potential
carbon
nitride
photocatalyst
(CN‐OA‐m)
can
be
tuned
by
changing
irradiation
wavelength
to
generate
electron
holes
different
oxidation
potentials.
This
tuning
was
key
realizing
photo‐chemo‐enzymatic
cascades
give
either
(
S
)‐
or
R
)‐enantiomer
phenylethanol.
In
combination
an
unspecific
peroxygenase
from
Agrocybe
aegerita
,
green
light
CN‐OA‐m
led
enantioselective
hydroxylation
ethylbenzene
)‐1‐phenylethanol
(99
%
ee
).
contrast,
blue
triggered
photocatalytic
acetophenone,
which
turn
enantioselectively
reduced
alcohol
dehydrogenase
Rhodococcus
ruber
form
(93
RSC Advances,
Journal Year:
2021,
Volume and Issue:
11(47), P. 29826 - 29858
Published: Jan. 1, 2021
DDQ
is
the
most
widely
used
quinone
with
a
high
reduction
potential
and
it
mediates
hydride
transfer
reactions
shows
three
accessible
oxidation
states:
(oxidized),
semiquinone
(one-electron-reduced)
hydroquinone
(two-electron-reduced).
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(2), P. 514 - 518
Published: Jan. 5, 2021
The
cleavage
of
benzyl
ethers
by
catalytic
hydrogenolysis
or
Birch
reduction
suffers
from
poor
functional
group
compatibility
and
limits
their
use
as
a
protecting
group.
visible-light-mediated
debenzylation
disclosed
here
renders
temporary
protective
groups,
enabling
new
orthogonal
protection
strategies.
Using
2,3-dichloro-5,6-dicyano-1,4-benzoquinone
(DDQ)
stoichiometric
photooxidant,
can
be
cleaved
in
the
presence
azides,
alkenes,
alkynes.
reaction
time
reduced
hours
to
minutes
continuous
flow.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(10), P. 6476 - 6488
Published: March 3, 2023
Four-membered
heterocycles
offer
exciting
potential
as
small
polar
motifs
in
medicinal
chemistry
but
require
further
methods
for
incorporation.
Photoredox
catalysis
is
a
powerful
method
the
mild
generation
of
alkyl
radicals
C–C
bond
formation.
The
effect
ring
strain
on
radical
reactivity
not
well
understood,
with
no
studies
that
address
this
question
systematically.
Examples
reactions
involve
benzylic
are
rare,
and
their
challenging
to
harness.
This
work
develops
functionalization
oxetanes
azetidines
using
visible
light
photoredox
prepare
3-aryl-3-alkyl
substituted
derivatives
assesses
influence
heterosubstitution
small-ring
radicals.
3-Aryl-3-carboxylic
acid
suitable
precursors
tertiary
oxetane/azetidine
which
undergo
conjugate
addition
into
activated
alkenes.
We
compare
oxetane
other
systems.
Computational
indicate
Giese
additions
unstrained
acrylates
reversible
result
low
yields
dimerization.
Benzylic
part
strained
ring,
however,
less
stable
more
π-delocalized,
decreasing
dimer
increasing
product
Oxetanes
show
high
due
Bent's
rule
rendering
irreversible.
ACS Catalysis,
Journal Year:
2021,
Volume and Issue:
11(21), P. 13337 - 13347
Published: Oct. 19, 2021
We
report
a
catalytic
method
for
the
direct
deoxygenation
of
various
C–O
bond-containing
functional
groups.
Using
Ni(II)
pre-catalyst
and
silane
reducing
agent,
alcohols,
epoxides,
ethers
are
reduced
to
corresponding
alkane.
Unsaturated
species
including
aldehydes
ketones
also
deoxygenated
via
initial
formation
an
intermediate
silylated
alcohol.
The
reaction
is
chemoselective
C(sp3)–O
bonds,
leaving
amines,
anilines,
aryl
ethers,
alkenes,
nitrogen-containing
heterocycles
untouched.
Applications
toward
deuteration,
benzyl
ether
deprotection,
valorization
biomass-derived
feedstocks
demonstrate
some
practical
aspects
this
methodology.
