Green Synthesis and Catalysis,
Год журнала:
2022,
Номер
5(1), С. 68 - 72
Опубликована: Дек. 14, 2022
A
novel,
efficient
and
pragmatic
method
to
prepare
gem-diboron
products
with
vicinal
tertiary/quaternary
stereocenters
using
LiTMP-mediated
1,6-conjugate
addition
of
gem-diborylalkanes
para-quinone
methides
was
described
for
the
first
time.
The
results
showed
that
various
tertiary
quaternary
could
be
formed
within
15
min
at
ambient
temperature.
This
simple
protocol
has
also
been
applied
synthesis
analogue
Bedaquiline.
Angewandte Chemie,
Год журнала:
2024,
Номер
136(25)
Опубликована: Апрель 11, 2024
Abstract
While
polyborylated
alkenes
are
being
recognized
for
their
elevated
status
as
highly
valuable
reagents
in
modern
organic
synthesis,
allowing
efficient
access
to
a
diverse
array
of
transformations,
including
the
formation
C−C
and
C‐heteroatom
bonds,
potential
energy‐transfer
reactive
groups
has
remained
unexplored.
Yet,
this
holds
key
generating
elusive
biradical
species,
which
can
be
captured
by
olefins,
thereby
leading
construction
new
highly‐borylated
scaffolds.
Herein,
we
report
designed
strategy
photosensitized
[2+2]‐cycloadditions
poly‐borylated
with
various
olefins
enabling
regioselective
synthesis
cyclobutane
motifs,
1,1‐di‐,
1,1,2‐tri‐,
1,1,2,2‐tetra‐borylated
cyclobutanes.
In
fact,
these
compounds
belong
family
that
presently
lacks
synthetic
pathways.
Interestingly,
when
α‐methylstyrene
was
used,
reaction
involves
an
interesting
1,5‐hydrogen
atom
transfer
(HAT).
Mechanistic
deuterium‐labeling
studies
have
provided
insight
into
outcome
process.
addition,
cyclobutanes
then
demonstrated
useful
selective
oxidation
processes
resulting
cyclobutanones
γ‐lactones.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(14), С. 2416 - 2421
Опубликована: Июнь 27, 2023
Abstract
A
dehydrogenative
fluorination
method
is
developed
to
access
multi‐substituted
trifluoromethylalkenes
starting
from
a
variety
of
gem
‐difluoroalkenes.
The
reaction
proceeds
with
electrophilic
source
NFSI
only
and
accommodates
wide
range
functional
groups,
thus
complementing
the
previously
reported
protocols.
Additionally,
visible‐light‐promoted
stereoinversion
revealed
enable
E
‐isomer
enriched
products.
Synthesis,
Год журнала:
2023,
Номер
55(22), С. 3799 - 3808
Опубликована: Авг. 2, 2023
Abstract
gem-Diborylalkanes
have
recently
emerged
as
valuable
synthons
for
diverse
C–C
bond-forming
reactions.
They
represent
an
important
class
of
bifunctional
reagents
that
can
be
applied
the
synthesis
simple
to
complex
skeletons.
Herein,
we
report
a
Pd-catalysed
hydrogenation
method
gem-diborylalkanes
from
corresponding
gem-diborylalkenes,
which
are
themselves
prepared
aldehydes
and
ketones
using
known
procedures.
In
addition,
transformations
two
representative
gem-diborylalkane
products
discussed
leading
range
functionalised
derivatives.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(43), С. 8658 - 8662
Опубликована: Янв. 1, 2023
We
present
a
blueprint
for
the
amination
and
defluoroamidation
of
α-trifluoromethylstyrene.
This
practical
protocol
presents
general
method
diversity-oriented
synthesis
vicinal
trifluoromethyl
amines
gem-difluoro
alkenes
from
α-trifluoromethylstyrene
maintaining
excellent
chemoselectivity.
The
synthetic
strategy
features
outstanding
atom
economy
wide
functional
group
tolerance
under
mild
reaction
conditions.
Green Synthesis and Catalysis,
Год журнала:
2022,
Номер
5(1), С. 68 - 72
Опубликована: Дек. 14, 2022
A
novel,
efficient
and
pragmatic
method
to
prepare
gem-diboron
products
with
vicinal
tertiary/quaternary
stereocenters
using
LiTMP-mediated
1,6-conjugate
addition
of
gem-diborylalkanes
para-quinone
methides
was
described
for
the
first
time.
The
results
showed
that
various
tertiary
quaternary
could
be
formed
within
15
min
at
ambient
temperature.
This
simple
protocol
has
also
been
applied
synthesis
analogue
Bedaquiline.
