Ir-Catalyzed, Nitrogen-Directed C(sp3)–H and C(sp2)–H Borylation with a Spiro-Fluorene-Indenoindenyl Ligand
Tomonori Inoue,
No information about this author
Yu Sato,
No information about this author
Yuki Nagashima
No information about this author
et al.
ACS Catalysis,
Journal Year:
2025,
Volume and Issue:
unknown, P. 4061 - 4068
Published: Feb. 21, 2025
Language: Английский
Metal‐Free Stereoconvergent C−H Borylation of Enamides
Tianhang Wang,
No information about this author
Zhengjun Wang,
No information about this author
Minyan Wang
No information about this author
et al.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(44)
Published: Sept. 18, 2023
Enamides,
functional
derivatives
of
enamines,
play
a
significant
role
as
synthetic
targets.
However,
the
stereoselective
synthesis
these
molecules
has
posed
longstanding
challenge
in
organic
chemistry,
particularly
for
acyclic
enamides
that
are
less
thermodynamically
stable.
In
this
study,
we
present
general
strategy
constructing
β-borylenamides
by
C-H
borylation,
which
provides
versatile
platform
generating
stereodefined
enamides.
Our
approach
involves
utilization
metalloid
borenium
cation,
generated
through
reaction
BBr3
and
presence
two
different
additives,
avoiding
any
exogenous
catalyst.
Importantly,
stereoconvergent
nature
methodology
allows
use
starting
materials
with
mixed
E/Z
configurations,
thus
highlighting
unique
advantage
chemistry.
Mechanistic
investigations
have
shed
light
on
pivotal
roles
played
reactive
boron
species,
phenomenon
stereoconvergence.
Language: Английский
Metal-Free ortho C–H Borylation of Thiobenzamides
Jianxing Lv,
No information about this author
Yixuan Liang,
No information about this author
Y. OUYANG
No information about this author
et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(18), P. 3709 - 3714
Published: May 1, 2024
A
BBr3-mediated
S-directed
ortho
C–H
borylation
of
thiobenzamides
was
developed.
variety
ortho-borylated
were
obtained
in
moderate
to
good
yields
with
a
wide
functional
group
tolerance
under
simple
and
metal-free
conditions.
This
transformation
provided
convenient
practical
route
important
functionalized
thiobenzamides.
Language: Английский
BX3-mediated borylation for the synthesis of organoboron compounds
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(23), P. 6010 - 6020
Published: Jan. 1, 2023
This
review
summarizes
the
recent
progress
in
borylation
driven
by
BX
3
fields
of
organic
synthesis
and
drug
synthesis.
Language: Английский
BBr3-Mediated ortho C–H Borylation of Benzamides
Yixuan Liang,
No information about this author
Chengyu Du,
No information about this author
C. Dong
No information about this author
et al.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 25, 2025
We
have
developed
a
BBr3-mediated,
metal-free
ortho
C-H
borylation
of
benzamides,
enabling
the
synthesis
wide
range
ortho-borylated
benzamides
in
moderate
to
good
yields.
This
transformation
offers
convenient
strategy
for
accessing
functionalized
which
are
valuable
intermediates
pharmaceuticals,
agrochemicals,
and
fine
chemical
synthesis.
Language: Английский
Regioselective ortho halogenation of N-aryl amides and ureas via oxidative halodeboronation: harnessing boron reactivity for efficient C–halogen bond installation
Chemical Science,
Journal Year:
2023,
Volume and Issue:
14(46), P. 13429 - 13436
Published: Jan. 1, 2023
The
installation
of
the
C-halogen
bond
at
ortho
position
N-aryl
amides
and
ureas
represents
a
tool
to
prepare
motifs
that
are
ubiquitous
in
biologically
active
compounds.
To
construct
such
prevalent
bonds,
most
methods
require
use
precious
metals
multistep
process.
Here
we
report
novel
protocol
for
long-standing
challenge
regioselective
halogenation
using
an
oxidative
halodeboronation.
By
harnessing
reactivity
boron
over
nitrogen,
merge
carbonyl-directed
borylation
with
consecutive
halodeboronation,
enabling
precise
introduction
C-X
desired
ureas.
This
method
offers
efficient,
practical,
scalable
solution
synthesizing
halogenated
N-heteroarenes
under
mild
conditions,
highlighting
superiority
directing
regioselectivity
reaction.
Language: Английский
Ortho Arylation of N‐Aryl Amides and the Construction of Diagonal Tetraarylbenzenediamines and N‐Doped Fulminenes via BBr3‐Derived Dibromoboracycles
Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
31(8)
Published: Nov. 8, 2024
The
synthesis
of
biaryl
amides,
which
are
prevalent
motifs
in
bioactive
molecules,
often
necessitates
lengthy
and
inefficient
procedures.
To
address
these
limitations,
catalytic
C-H
activation
protocols
have
emerged,
enabling
the
direct
ortho-arylation
aryl
amides.
However,
suffer
from
issues
such
as
lack
selectivity,
reliance
on
stoichiometric
oxidants,
requirement
for
excess
reagents
harsh
reaction
conditions.
overcome
challenges,
we
present
a
novel
highly
selective
protocol
N-aryl
amides
ureas.
high
selectivity
originates
directed
installation
BBr3
to
form
boracycle,
then
undergoes
cross-coupling
with
an
halide.
Our
method
offers
significant
advantages,
including
mild
conditions,
excellent
site-specificity,
scalability.
demonstrates
broad
compatibility
diverse
range
readily
accessible
functionalized
anilides
iodides,
evidenced
by
55
successful
examples
yielding
products
30-95
%
range.
Furthermore,
our
methodology
surpasses
conventional
approaches
facilitating
one-pot
diagonal
diarylation
dianilides.
This
capability
unlocks
construction
previously
unattainable
systems,
serve
valuable
precursors
tetraarylbenzenediamines
N-doped
fulminenes,
two
crucial
compound
classes
materials
science.
Language: Английский
Transforming cyclopropanes to enamides via σ-C–C bond eliminative borylation
Shuyu Kang,
No information about this author
Jiahang Lv,
No information about this author
Tianhang Wang
No information about this author
et al.
Nature Communications,
Journal Year:
2024,
Volume and Issue:
15(1)
Published: Aug. 27, 2024
Recent
strides
in
C–H
borylation
have
significantly
expanded
our
toolkit
for
the
preparation
of
organoboronates.
Nevertheless,
avenues
alternative
to
obtain
these
compounds
via
σ-C–C
cleavage,
thereby
facilitating
molecular
scaffold
editing,
remain
scarce.
Several
methodologies
been
proposed
hydroboration
cyclopropanes
by
activating
C–C
bonds,
conventionally
relying
on
noble
and
hazardous
metal
catalysts
control
reaction
outcomes.
Here,
we
present
a
strategy
crafting
stereochemically
precise
γ-borylenamides
through
ring-opening
avoiding
any
metallic
entities.
Boryl
species,
generated
ternary
with
BCl3,
cyclopropanes,
tertiary
amine,
selectively
undergo
bond
eliminative
under
directing
N-acyl
group,
ensuring
enhanced
selectivity
efficiency
along
pathway.
Such
inherently
stereoconvergent
approach
accommodates
precursors
diverse
geometries,
including
cis/trans
isomeric
blends.
authors
report
without
Language: Английский
Metal‐Free Stereoconvergent C−H Borylation of Enamides
Tianhang Wang,
No information about this author
Zhengjun Wang,
No information about this author
Minyan Wang
No information about this author
et al.
Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
135(44)
Published: Sept. 18, 2023
Abstract
Enamides,
functional
derivatives
of
enamines,
play
a
significant
role
as
synthetic
targets.
However,
the
stereoselective
synthesis
these
molecules
has
posed
longstanding
challenge
in
organic
chemistry,
particularly
for
acyclic
enamides
that
are
less
thermodynamically
stable.
In
this
study,
we
present
general
strategy
constructing
β‐borylenamides
by
C−H
borylation,
which
provides
versatile
platform
generating
stereodefined
enamides.
Our
approach
involves
utilization
metalloid
borenium
cation,
generated
through
reaction
BBr
3
and
presence
two
different
additives,
avoiding
any
exogenous
catalyst.
Importantly,
stereoconvergent
nature
methodology
allows
use
starting
materials
with
mixed
E/Z
configurations,
thus
highlighting
unique
advantage
chemistry.
Mechanistic
investigations
have
shed
light
on
pivotal
roles
played
reactive
boron
species,
phenomenon
stereoconvergence.
Language: Английский