Benzothiazolines Acting as Carbanion and Radical Transfer Reagents in Carbon–Carbon Bond Construction
Molecules,
Год журнала:
2025,
Номер
30(8), С. 1711 - 1711
Опубликована: Апрель 11, 2025
Traditionally
employed
as
hydrogenation
reagents,
benzothiazolines
have
emerged
versatile
carbanion
and
radical
transfer
playing
a
vital
role
in
the
construction
of
various
carbon-carbon
bonds.
The
cutting-edge
progress
photochemistry
chemistry
prompted
study
visible
light-driven
reactions,
bringing
into
vibrant
focus.
Their
chemical
processes
been
uncovered
to
encompass
variety
activation
mechanisms,
with
five
distinct
modes
having
identified.
This
work
reviews
innovative
applications
donors
alkyl
or
acyl
groups,
achieving
hydroalkylation
hydroacylation
substitution.
By
examining
their
diverse
this
review
highlights
potential
serving
groups
for
further
research
development.
Moreover,
will
offer
exemplary
inspiration
synthetic
chemists,
contributing
ongoing
evolution
utility
organic
synthesis.
Язык: Английский
Switching Mesoionic Carbene-Organocatalysis from Radical to Ionic Pathway through Base-Controlled Formation of Breslow Intermediates versus Breslow Enolates
Chemical Science,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
N-heterocyclic
carbene
(NHC)
organocatalysis
has
experienced
significant
advancements.
Two
distinct
reaction
pathways
have
been
developed,
ionic
and
radical,
through
Breslow
intermediates
(BIs)
enolates
(BI-s),
respectively.
The
ability
to
selectively
generate
these
is
crucial
for
optimizing
outcomes.
In
this
paper
we
show
that
with
mesoionic
carbenes
(MICs)
it
possible
control
the
formation
of
BIs
versus
BI-s,
use
weak
bases
strong
bases,
Of
particular
interest
coupling
aldehydes
alkyl
halides
yield
ketones
via
an
pathway.
Язык: Английский
Construction of C–S and C–Se Bonds via Photocatalytic Aromatization-Driven Deconstructive Diversification of Spiro-Dihydroquinazolinones Derived from Unstrained Ketones
Tao Wang,
Jin‐Long Dai,
Yifeng Jiang
и другие.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 13, 2025
A
novel
and
robust
deconstructive
functionalization
reaction
of
spiro-dihydroquinazolinones
with
sulfenylating
reagents
in
the
presence
base
has
been
realized
under
visible
light
irradiation.
This
enabled
direct
ring-opening
unstrained
cyclic
ring
systems,
producing
skeletally
diverse
functionalized
quinazolinones
moderate
to
good
yields.
range
variety
including
diaryl
disulfide,
thiosulfonate,
dithiosulfonate
1-[(trifluoromethyl)thio]-2,5-pyrrolidinedione
were
compatible
for
this
transformation.
In
addition,
diselenide
selenosulfonate
could
also
couple
form
C-Se
Bonds.
Mechanistic
studies
revealed
that
proceeds
via
a
radical-radical
coupling
pathway.
Язык: Английский
Redox-Paired Reductive Heck Reaction and Oxidative Esterification Catalyzed by Mesoionic Carbenes
Organic Letters,
Год журнала:
2024,
Номер
26(35), С. 7419 - 7424
Опубликована: Авг. 22, 2024
Paring
a
reductive
reaction
and
an
oxidative
in
one
could
be
immensely
important
achieving
atom
economic
environmental
advantages.
Herein,
we
report
simple
protocol
that
combines
two
such
Heck
reactions
esterification
by
using
mesoionic
carbenes
as
catalysts
to
synthesize
multiple
valuable
products
under
mild
conditions.
Язык: Английский
Cooperative Photoredox and N-Heterocyclic Carbene-Catalyzed Formal C-H Acylation of Cyclopropanes via Deconstruction-Reconstruction Strategy
Chemical Science,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
Cooperative
NHC/photoredox
catalyzed
deconstruction–reconstruction
of
aryl
cyclopropanes
was
described
to
access
various
α-acylated
cyclopropane
derivatives.
Язык: Английский
Ketone Skeletal Modification via a Metallaphotoredox-Catalyzed Deacylation and Acylation Strategy
Organic Letters,
Год журнала:
2024,
Номер
26(44), С. 9503 - 9507
Опубликована: Окт. 28, 2024
Herein,
we
describe
a
dual
catalytic
strategy
that
employs
dihydroquinazolinones,
derived
from
ketone
analogs,
as
versatile
intermediates
for
acylation
via
α
C–C
cleavage
with
2-pyridyl
esters,
facilitating
the
efficient
synthesis
of
variety
ketones.
The
reaction
accommodates
wide
range
ketones
and
carboxylic
acids,
showing
tolerance
to
various
functional
groups.
versatility
this
synthetic
technique
is
further
highlighted
through
its
application
in
late-stage
modification
pharmaceuticals
biologically
active
natural
products.
Язык: Английский
Electrochemical C H alkylation of N-heterocycles via aromatization-driven C C fragmentation of unstrained ketones
Tetrahedron Letters,
Год журнала:
2024,
Номер
155, С. 155440 - 155440
Опубликована: Дек. 27, 2024
Язык: Английский
Deuteration Degree Controllable Synthesis of Aryl Deuteromethyl Ethers Through Dual photoredox and Thiol Catalysis
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(62)
Опубликована: Авг. 22, 2024
Herein,
we
report
a
facile
and
efficient
deuteration
degree
controllable
method
for
the
preparation
of
aryl
deuteromethyl
ethers
through
dual
photoredox
thiol
catalysis
using
phenols
as
starting
materials
inexpensive
D
Язык: Английский
Photoredox decarboxylative acylation of carboxylic acid by 4-acyl-1,2,3-triazoliums
Green Synthesis and Catalysis,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 1, 2024
Язык: Английский
Revealing Dinitrogen Activation via Mesoionic Carbenes: A Computational Design with Frustrated Lewis Pairs
Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 13, 2024
Abstract
Activating
dinitrogen
under
metal‐free
conditions
remains
a
significant
challenge
in
chemistry.
In
this
study,
we
computationally
designed
frustrated
Lewis
pair
(FLP)
system
incorporating
bis(trimethylsilyl)boryl
substituent
on
mesoionic
carbene
(MIC)
framework.
Our
models
show
both
kinetic
and
thermodynamic
favorability
for
activation.
Aromaticity
enhancement
along
the
potential
energy
surface
(PES)
plays
critical
role
driving
reaction.
This
work
provides
insights
into
utilizing
main‐group
elements
activation
offers
applications
inert
molecule
optical
materials.
Язык: Английский