European Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
2022(25)
Published: May 19, 2022
Abstract
2‐(2‐(Benzylthio)benzylidene)malonates
can
undergo
the
1,5‐hydride
shift
triggered
cyclization
resulting
in
thiachromanes
45–84
%
yield.
Boron
trifluoride
as
a
reaction
promotor
is
key
to
success.
DFT
calculations
revealed
that
proceeds
via
chelate
BF2
complex,
which
was
confirmed
by
NMR‐analysis.
Experimental
and
theoretical
comparison
of
nitrogen,
sulfur
carbon
analogues
derivatives
have
highest
activation
barrier
for
hydride
transfer
due
unfavorable
transition
state
geometry,
explains
lack
previous
reports
on
shifts
(alkylthio)styrenes.
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.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(18), P. 5041 - 5052
Published: Jan. 1, 2022
This
review
highlights
the
encouraging
advances
in
hydride
transfer-involved
dearomatization
reaction
during
past
decade,
content
of
which
is
categorized
according
to
acceptors,
namely
vinylogous
imines
and
quinone
methides.
Organic Chemistry Frontiers,
Journal Year:
2020,
Volume and Issue:
7(17), P. 2511 - 2517
Published: Jan. 1, 2020
Hydride
transfer
enabled
the
first
success
of
regioselective
dearomatization
indoles
in
carbocyclic
ring
and
pyrrole
ring,
which
was
induced
by
ortho-quinone
methides
vinylogous
iminium
intermediates,
respectively.
Bulletin of the Chemical Society of Japan,
Journal Year:
2022,
Volume and Issue:
95(2), P. 296 - 305
Published: Jan. 12, 2022
Abstract
An
efficient
catalytic
internal
redox
reaction
(hydride
shift
mediated
C(sp3)–H
bond
functionalization)
has
been
developed,
which
the
following
salient
features:
(1)
functionalization,
(2)
Lewis
and/or
Brønsted
acid
catalyzed
(transition
metals
employed
in
conventional
C–H
functionalization
are
not
required),
and
(3)
construction
of
complex
polycycles
that
otherwise
difficult
to
synthesize
by
methods.
Our
recent
efforts
on
development
novel
types
hydride
shift/cyclization
system
described.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(14), P. 2432 - 2437
Published: April 5, 2023
An
unprecedented
hydride
transfer-triggered
cross-dehydrogenative
coupling
of
two
C(sp3)-H
bonds
to
target
nine-membered
rings
has
been
developed.
Salient
features
this
methodology
include
atom
and
step
economy
metal-free
redox-neutral
conditions,
with
water
as
the
byproduct
proceeding
well
even
decomposed
aldehydes.
Green Chemistry,
Journal Year:
2021,
Volume and Issue:
23(20), P. 8181 - 8186
Published: Jan. 1, 2021
An
unprecedented
organocatalytic
cascade
aldimine
condensation/[1,6]-hydride
transfer/Mannich-type
cyclization
of
indole-2-carbaldehydes
with
o
-aminoanilines
was
developed
to
assemble
indole-2,3-fused
diazocanes
in
one
step.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(3), P. 1753 - 1761
Published: Jan. 22, 2024
A
novel
and
flexible
domino
reaction
of
aurones
with
pyridin-2-yl
active
methylene
compounds
promoted
by
I2/BF3
has
been
developed
to
afford
spirodihydroindolizines
indolizines
in
a
controllable
manner.
When
the
was
performed
1,2-dichloroethane
at
80
°C,
variety
were
obtained,
whereas
it
almost
exclusively
provided
series
when
mixed
solvent
N,N-dimethylformamide
relatively
higher
temperature
100
°C.
Being
metal-free,
excellent
product
selectivity,
high
atom
economy,
good
functional
group
tolerance,
feasibility
for
large-scale
synthesis
are
salient
features
methodology.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(23), P. 9100 - 9105
Published: Nov. 12, 2021
A
cascade
aldimine
condensation/1,6-hydride
transfer/Mannich-type
cyclization
of
indole-derived
phenylenediamine
with
aldehydes
was
developed
for
one-step
construction
a
polycyclic
indole-3,4-fused
skeleton.
Aldehyde
serves
as
key
to
start
the
whole
process,
including
1,6-hydride
transfer
enabled
δ-C(sp3)–H
activation
secondary
amine.
The
challenges
medium-sized
rings
are
addressed
via
hydride
chemistry.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(2), P. 450 - 455
Published: Jan. 8, 2024
δ-Hydroxy
chloronitroso
compounds
generated
in
situ
from
1,2-oxazine
N-oxides
undergo
a
1,5-hydride
transfer
related
to
the
Meerwein–Ponndorf–Verley–Oppenauer
reaction.
Based
on
process
discovered,
three-step
access
fused
pyrrolidine
scaffolds
containing
up
four
contiguous
stereogenic
centers
starting
simple
nitrostyrenes
and
cycloalkenes
or
cyclodienes
has
been
developed.
The
suggested
reaction
mechanism
was
confirmed
by
UV–vis
ATR
FT-IR
monitoring
DFT
calculations.
