Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(2), P. 442 - 448
Published: Jan. 6, 2021
Highly
enantio-
and
regioselective
(3
+
2)
formal
cycloaddition
of
β-substituted
ene-
thioenecarbamates
as
well
cyclic
enamides
with
quinone
diimides
catalyzed
by
a
BINOL-
SPINOL-derived
phosphoric
acid
is
reported.
A
wide
variety
2,3-disubstituted
2-aminoindolines,
including
polycyclic
ones,
were
prepared
in
generally
high
yields
(up
to
98%)
moderate
complete
diastereoselectivities
most
cases
excellent
enantioselectivities
99%
ee).
Organic & Biomolecular Chemistry,
Journal Year:
2020,
Volume and Issue:
18(44), P. 8939 - 8974
Published: Jan. 1, 2020
This
review
systematically
outlined
the
research
in
area
of
transition
metal
free
synthesis
alkyl
pinacol
boronates,
which
are
versatile
and
important
scaffolds
to
construct
diverse
organic
compounds.
Angewandte Chemie International Edition,
Journal Year:
2019,
Volume and Issue:
59(8), P. 3294 - 3299
Published: Nov. 29, 2019
A
new
chiral
Brønsted
acid,
generated
in
situ
from
a
phosphoric
acid
boron
(CPAB)
complex
and
water,
was
successfully
applied
to
asymmetric
indole
reduction.
This
"designer
catalyst",
which
is
more
acidic
than
TsOH
as
suggested
by
DFT
calculations,
allows
the
unprecedented
direct
reduction
of
C2-aryl-substituted
N-unprotected
indoles
features
good
excellent
enantioselectivities
with
broad
functional
group
tolerance.
calculations
mechanistic
experiments
indicates
that
this
reaction
undergoes
C3-protonation
hydride-transfer
processes.
Besides,
bulky
C2-alkyl-substituted
are
also
suitable
for
system.
Angewandte Chemie International Edition,
Journal Year:
2019,
Volume and Issue:
58(16), P. 5392 - 5395
Published: March 1, 2019
Organic
chemists
now
can
construct
carbon-carbon
σ-bonds
selectively
and
sequentially,
whereas
methods
for
the
selective
cleavage
of
σ-bonds,
especially
unreactive
hydrocarbons,
remain
limited.
Activation
by
ring
strain,
directing
groups,
or
in
presence
a
carbonyl
cyano
group
is
usually
required.
In
this
work,
using
sequential
strategy
site-selective
borylation
C(aryl)-CH3
bonds
has
been
developed
under
free
transition
metal
conditions.
Methyl
groups
various
arenes
are
cleaved
replaced
boryl
groups.
Mechanistic
analysis
suggests
that
it
proceeds
intermolecular
oxidation
coupling
transient
aryl
radical,
generated
radical
decarboxylation,
involving
pyridine-stabilized
persistent
radical.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(52)
Published: Oct. 31, 2022
Transition-metal-catalyzed
Suzuki-Miyaura
coupling
has
significantly
advanced
C-C
bond
formation
and
been
well
recognized
in
organic
synthesis,
pharmaceuticals,
materials
science
other
fields.
In
this
rapid
development,
cross
without
transition
metal
catalyst
is
a
big
challenge
field,
using
widely
existing
tertiary
amines
as
electrophiles
to
directly
couple
with
boronic
acids
great
hurdles
yet
significant
application
prospects.
Herein,
we
report
an
efficient
general
deaminative
arylation
alkenylation
of
(propargyl
amines,
allyl
1H-indol-3-yl
methane
amines)
ary
alkenylboronic
enabled
by
difluorocarbene
under
transition-metal-free
conditions.
Preliminary
mechanism
experiments
suggest
that
situ
formed
difluoromethyl
quaternary
amine
salt,
nitrogen
ylide
tetracoordinate
boron
species
are
the
key
intermediates,
subsequent
1,2-metallate
shift
protodeboronation
complete
new
reaction.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(2), P. 442 - 448
Published: Jan. 6, 2021
Highly
enantio-
and
regioselective
(3
+
2)
formal
cycloaddition
of
β-substituted
ene-
thioenecarbamates
as
well
cyclic
enamides
with
quinone
diimides
catalyzed
by
a
BINOL-
SPINOL-derived
phosphoric
acid
is
reported.
A
wide
variety
2,3-disubstituted
2-aminoindolines,
including
polycyclic
ones,
were
prepared
in
generally
high
yields
(up
to
98%)
moderate
complete
diastereoselectivities
most
cases
excellent
enantioselectivities
99%
ee).
