Angewandte Chemie International Edition,
Journal Year:
2017,
Volume and Issue:
56(28), P. 8163 - 8167
Published: May 17, 2017
Abstract
Rhodium(III)‐
and
cobalt(III)‐catalyzed
C−H
activation
of
indoles
coupling
with
1,6‐enynes
is
discussed.
Under
rhodium(III)
catalysis,
the
alkyne
insertion
follows
2,1‐regioselectivity
a
subsequent
type‐I
intramolecular
Diels–Alder
reaction
(IMDA)
to
afford
[6,5]‐fused
cycles.
When
catalyzed
by
cobalt(III)
congener,
1,2‐insertion
preferred,
followed
rare
type‐II
IMDA,
thus
leading
bridged
[3,3,1]‐cycles.
This
selectivity
was
mainly
tuned
steric
sensitivity
catalyst.
Chemical Reviews,
Journal Year:
2016,
Volume and Issue:
116(16), P. 9091 - 9161
Published: July 19, 2016
Although
known
for
over
90
years,
only
in
the
past
two
decades
has
chemistry
of
diboron(4)
compounds
been
extensively
explored.
Many
interesting
structural
features
and
reaction
patterns
have
emerged,
more
importantly,
these
now
feature
prominently
both
metal-catalyzed
metal-free
methodologies
formation
B-C
bonds
other
processes.
Chemical Reviews,
Journal Year:
2016,
Volume and Issue:
116(12), P. 7330 - 7396
Published: June 2, 2016
This
Review
summarizes
the
advances
in
construction
of
all-carbon
quaternary
stereocenters
via
catalytic
enantioselective
desymmetrization
prochiral
and
meso-compounds,
highlights
power
potential
this
strategy
total
synthesis
natural
products
biologically
active
compounds,
outlines
synthetic
opportunities
still
available.
ACS Catalysis,
Journal Year:
2016,
Volume and Issue:
6(3), P. 1799 - 1811
Published: Feb. 3, 2016
Alkenylboranes
have
been
vital
reagents
in
modern
synthetic
organic
chemistry,
whose
carbon–boron
bond
is
transformable
into
a
carbon–carbon
stereoretentively
to
give
such
invaluable
mutisubstituted
alkenes
as
natural
products,
biologically
active
molecules,
and
functional
materials.
Introduction
of
boryl
moiety
across
triple
alkynes
(borylation
alkynes)
one
the
most
direct
potent
methods
for
synthesizing
alkenylboranes,
this
field
has
thus
far
experienced
remarkable
progress
mainly
with
group
10
transition
metal
catalysts
(Ni,
Pd,
Pt),
which
enables
highly
functionalized
alkenylboranes
be
constructed
stereoselectively.
On
other
hand,
much
attention
recently
focused
on
appealing
catalysis
base
(Fe,
Co)
coinage
(Cu,
Ag,
Au)
metals
toward
borylation
alkynes,
summarized
perspective.
Chemical Society Reviews,
Journal Year:
2018,
Volume and Issue:
47(19), P. 7477 - 7494
Published: Jan. 1, 2018
The
diverse
applications
of
copper-catalyzed
borylation,
which
has
become
an
essential
strategy
in
modern
synthetic
organic
chemistry,
are
reviewed
and
illustrated.
Journal of the American Chemical Society,
Journal Year:
2015,
Volume and Issue:
137(43), P. 13760 - 13763
Published: Oct. 13, 2015
A
cooperative
Cu/Pd-catalyzed
asymmetric
three-component
reaction
of
styrenes,
B2(pin)2,
and
allyl
carbonates
was
reported.
This
reaction,
in
the
presence
chiral
CuOAc/SOP
achiral
Pd(dppf)Cl2
catalysts,
occurs
smoothly
with
high
enantioselectivities
(up
to
97%
ee)
.
The
allylboration
products,
which
contain
alkene
(or
diene)
unite
alkylboron
group,
are
easily
functionalized.
utility
this
protocol
demonstrated
through
synthesis
an
antipsychotic
drug,
(−)-preclamol.
Angewandte Chemie International Edition,
Journal Year:
2014,
Volume and Issue:
53(13), P. 3475 - 3479
Published: Feb. 14, 2014
Abstract
Copper‐catalyzed
Suzuki–Miyaura‐type
cross‐coupling
and
carboboration
processes
are
reported.
The
cross‐couplings
function
well
with
a
variety
of
substituted
aryl
iodides
boronic
esters
allows
for
orthogonal
reactivity
compared
to
palladium‐catalyzed
processes.
method
includes
both
alkynes
allenes
provides
access
highly
stereodefined
vinyl
esters.
alkyne
is
highlighted
in
the
simple
one‐pot
synthesis
Tamoxifen.
Journal of the American Chemical Society,
Journal Year:
2015,
Volume and Issue:
137(28), P. 8928 - 8931
Published: July 1, 2015
A
catalytic
domino
spirocyclization
of
1,7-enynes
with
simple
cycloalkanes
and
cyclo-1,3-dicarbonyls
has
been
established
via
multiple
C-C
bond
formations
from
alkynyl/alkenyl
functions
dual
α,α-C(sp(3))-H
abstraction/insertion.
The
reaction
involves
addition,
6-exo-dig
cyclization
radical
coupling
sequences
under
convenient
conditions
provides
a
concise
access
to
spiro
cyclopenta[c]quinolines
in
good
excellent
yields.
ACS Catalysis,
Journal Year:
2020,
Volume and Issue:
10(19), P. 11578 - 11622
Published: Aug. 25, 2020
Organoboronates
represent
a
cornerstone
functional
group
in
modern
synthesis
owing
to
their
unique
reactivity
and
divergent
synthetic
capability.
Copper
catalysis
has
become
one
of
the
most
powerful
methods
stereoselectively
install
boron
across
diverse
π-systems.
Additionally,
this
method
affords
tremendous
versatility
enabled
by
difunctionalization
π-system
addition
an
electrophile.
This
review
covers
known
electrophiles
intercept
catalytic
intermediates
borylative
strategies
that
have
been
reported
up
end
May
2020.
Journal of the American Chemical Society,
Journal Year:
2014,
Volume and Issue:
136(44), P. 15607 - 15614
Published: Oct. 13, 2014
Two
tunable
arylative
cyclizations
of
cyclohexadienone-containing
1,6-enynes
are
reported
via
rhodium(III)-catalyzed
C–H
activation
O-substituted
N-hydroxybenzamides.
The
use
different
O
substituents,
i.e.
O-Piv
and
O-Me,
on
the
directing
group
allows
formation
either
tetracyclic
isoquinolones
through
an
Ⓝ-Michael
addition
process
or
hydrobenzofurans
a
Ⓒ-Michael
process.
Mechanistic
investigations
these
two
cascade
reactions
clearly
indicated
that
bond
cleavage
was
involved
in
turnover-limiting
step.
Furthermore,
cyclization
products
could
be
subjected
to
various
transformations
for
elaborating
pharmaceutically
synthetically
valuable
potential.
This
is
first
example
reaction
1,6-enynes,
results
extend
application
realm
Cp*RhIII-catalyzed
reactions.
