Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(27)
Published: March 29, 2024
Abstract
Inverse
hydride
shuttle
catalysis
provides
a
multicomponent
platform
for
the
highly
efficient
synthesis
of
alkaloid
frameworks
with
exquisite
diastereoselectivity.
However,
number
limitations
hinder
this
method,
primarily
strict
requirement
electron‐deficient
acceptors.
Herein,
we
present
general
Lewis
acid‐driven
approach
to
address
constraint,
and
have
developed
two
broad
strategies
enabling
modular
complex
azabicycles
that
were
entirely
unattainable
using
previous
method.
The
enhanced
synthetic
flexibility
facilitates
streamlined
asymmetric
cyclization,
leading
concise
total
(−)‐tashiromine.
Organic Chemistry Frontiers,
Journal Year:
2020,
Volume and Issue:
7(13), P. 1743 - 1778
Published: Jan. 1, 2020
In
this
review,
we
provide
a
comprehensive
overview
of
recent
progress
in
rapidly
growing
field
by
summarizing
the
1,6-conjugate
addition
and
annulation
reactions
p-QMs
with
consideration
their
mechanisms
applications.
European Journal of Organic Chemistry,
Journal Year:
2020,
Volume and Issue:
2020(18), P. 2650 - 2692
Published: Feb. 28, 2020
para
‐Quinone
methides
(
p
‐QMs)
are
naturally
occurring
molecules
that
have
been
finding
increasing
synthetic
applications
in
the
last
few
years.
The
presence
of
two
electronically
different
exocyclic
conjugate
substituents
their
structure,
carbonyl
and
methylidene,
leads
to
a
pronounced
reactivity
owing
polarization
molecule.
In
this
sense,
those
prone
undergo
attack
nucleophiles
terminal
carbon
double
bond,
behaving
as
vinylogous
electrophiles
generating
1,6‐addition
products.
context,
years
development
catalytic
approaches
for
1,6‐nucleophilic
addition
reactions
involving
‐QMs
has
attracted
considerable
attention.
Considering
extensive
such
found
decades
reactions,
review
we
comprehensively
discuss
historical
field,
starting
with
early
on
natural
product
synthesis,
going
through
seminal
non‐stereoselective
processes
progressing
cutting‐edge
asymmetric‐catalyzed
approaches.
Journal of the American Chemical Society,
Journal Year:
2019,
Volume and Issue:
141(37), P. 14570 - 14575
Published: Sept. 3, 2019
An
efficient
deuteration
process
of
β-amino
C–H
bonds
in
various
N-alkylamine-based
pharmaceutical
compounds
has
been
developed.
Catalytic
reactions
begin
with
the
action
Lewis
acidic
B(C6F5)3
and
Brønsted
basic
N-alkylamine,
converting
a
drug
molecule
into
corresponding
enamine.
The
acid/base
catalysts
also
promote
dedeuteration
acetone-d6
to
afford
deuterated
ammonium
ion.
Ensuing
enamine
then
leads
formation
β-deuterated
bioactive
amines
up
99%
deuterium
incorporation.
Organic Chemistry Frontiers,
Journal Year:
2021,
Volume and Issue:
8(6), P. 1364 - 1383
Published: Jan. 1, 2021
This
review
summarizes
the
recent
progresses
(2016–2020)
in
hydride
transfer-enabled
C(sp3)–H
activation
according
to
reaction
types,
categorized
into
intramolecular/intermolecular
functionalization,
and
reduction.
Chemical Society Reviews,
Journal Year:
2020,
Volume and Issue:
50(3), P. 1945 - 1967
Published: Dec. 16, 2020
In
contrast
to
transition
metal-catalysed
C-H
functionalisation,
highly
efficient
construction
of
C-C
and
C-X
(X
=
N,
O,
S,
B,
Si,
etc.)
bonds
through
metal-free
catalytic
functionalisation
remains
one
the
most
challenging
tasks
for
synthetic
chemists.
recent
years,
electron-deficient
boron-based
catalyst
systems
have
exhibited
great
potential
bond
transformations.
Such
emerging
may
greatly
enrich
chemistry
main-group
element
catalysis,
will
also
provide
enormous
opportunities
in
chemistry,
materials
chemical
biology.
This
article
aims
give
a
timely
comprehensive
overview
recognise
current
status
catalysis
stimulate
development
more
systems.
Chemical Society Reviews,
Journal Year:
2021,
Volume and Issue:
50(6), P. 3720 - 3737
Published: Jan. 1, 2021
Borane
mediated
hydride
abstraction
of
amines
efficiently
generates
useful
iminium
salts.
This
review
explores
this
fascinating
reactivity
and
discusses
how
the
intermediates
are
utilised
in
a
variety
stoichiometric
catalytic
processes.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(7), P. 4856 - 4864
Published: March 18, 2024
Pyrroles
are
important
N-heterocycles
found
in
medicines
and
materials.
The
formation
of
pyrroles
from
widely
accessible
pyrrolidines
is
a
potentially
attractive
strategy
but
an
underdeveloped
approach
due
to
the
sensitivity
oxidative
conditions
required
achieve
such
transformation.
Herein,
we
report
catalytic
that
employs
commercially
available
B(C6F5)3
operationally
simple
procedure
allows
serve
as
direct
synthons
for
pyrroles.
Mechanistic
studies
have
revealed
insights
into
borane-catalyzed
dehydrogenative
processes.
Chemical Science,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
A
dual
relay
catalytic
protocol,
built
on
reversible
dehydrogenation
of
amines
by
Rh
catalysis
and
C-H
functionalisation
transient
imines
Pd
catalysis,
is
reported
to
enable
regioselective
arylation
at
their
unactivated
β-C(sp3)-H
bond.
Notably,
the
new
strategy
applicable
secondary
anilines
N-PMP-protected
primary
aliphatic
intermediate
steric
demands,
which
in
contrast
existing
strategies
that
involve
either
free-amine-directed
activation
for
highly
sterically
hindered
or
steric-controlled
migrative
cross-coupling
unhindered
N-Boc
protected
amines.
Regioselectivity
reaction
imposed
electronic
effects
imine
intermediates
rather
than
between
specific
starting
materials
catalysts,
thereby
opening
uncharted
scope
In
a
broader
sense,
this
study
demonstrates
opportunities
involving
hydrogen
borrowing
chemistry,
previously
explored
alcohols,
execute
otherwise
challenging
transformations
amines,
commonly
present
natural
products,
pharmaceuticals,
biologically
active
molecules,
functional
materials.
