Perfluoroalkylation Reactions by Electron Donor‐Acceptor Complexes: Recent Advances
ChemPhotoChem,
Год журнала:
2024,
Номер
8(8)
Опубликована: Май 3, 2024
Abstract
This
Perspective
analyses
the
perfluoroalkylation
reactions
by
electron
donor‐acceptor
(EDA)
complexes
since
2018,
while
summarizes,
in
Tables
,
vast
majority
of
representative
various
classes
organic
compounds
EDA
and
halogen‐bonding
interactions.
Numerous
intriguing
reaction
methodologies
valuable
synthetic
instances
have
emerged.
We
aim
to
delve
into
these
new
examples
comprehensively,
also
contemplating
future
directions
field.
Subsequent
sections
will
elaborate
on
(hetero)aromatic
compounds,
carbon‐carbon
multiple
bonds,
carbonyl
isocyanides,
covering
their
scope
mechanistic
insights.
Perfluoroalkylation
complexes.
Entry
Substrate
Complex
Reaction
conditions
Product
Ref.
1
[13]
2
[46]
3
R
F
I
(3
equiv.)
KOH
(1.5
Blue
LEDs
H
O,
Ar,
20
h
[47]
4
TEEDA
CFL
(25
W)
THF,
r.t.
F−
[48]
5
ICF
CO
Et
(1.3
Na
DMSO
mL)
rt.
427
nm
LED,
16
[49]
6
TMG
(2.5
23
W
CFL,
MeCN/Hex
f
(5
:
1)
[42,50]
7
MeCN
[51]
8
Umemoto's
reagent
(2
N
‐methylmorpholine
DMF,
[52]
9
Cs
white
light
O
r.t.,
[53]
10
4.5
450
laser
CaCl
MeNO
0
°C
[3]
11
t
‐BuONa
DMF
Green
[54]
12
or
complex
I−R
(2.1
TMEDA
DBU
24
[55,56]
13
TFE/water
(1
(0.2
M)
CF
SO
[84]
bonds
constrained
cyclic
Bu
NCl,
Hg
lamp
(6
(1.2
CH
OH,
1.5
r.t,
Ar
[39]
[57]
DIPEA
……..
−I
Base
THF
25
with
DIPEA,
TEEDA;
[48,58,59]
Bn
NH
[60]
Base,
[61]
O/toluene=9
LEDs,
65
°C,
[41]
K
PO
CuCl
(10
mol%)
TMSNCS
CN
Violet
(24
[37]
Diphenylacetaldehyde
Pyrrolidine
(40
DCE
mL);
(0.8
eq.);
White
W);
[44,62]
DIPEA,DMA
(trace
air)
36–72
[63]
n
‐C
air,
RT
[64]
DABCO
υ
(400
Watt)
50
C
2n+1
(1.8
[65–67]
DCE,
[27]
14
2,4,6‐trimethylpyridine
MeCN,
60
Togni's
[68]
15
PMDETA
[69]
[70,71]
17
less
than
%
water
mmol)
isocyanides
hydrazones.
[72,73]
cis
‐catalyst
M
(20
2,6‐lutidine
(0.7
‐10
[74]
[75]
phase
transfer
catalyst
Cl/8F
18
1),
[32]
ambient
NaOH
(4.1
R.T.
[76]
36
30
[77]
I−C
[78]
[79]
Imidazole
[80]
Язык: Английский
Recent Progress in C–S Bond Formation via Electron Donor-Acceptor Photoactivation
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
This
review
summarizes
recent
progress
in
EDA
complex-promoted
C–S
bond
formation
using
various
sulfur-containing
substrates
under
mild
conditions
via
visible
light
irradiation.
Язык: Английский
Electrochemical Trifluoromethylation of Alkynes: The Unique Role of DMSO as a Masking Auxiliary
Chemical Science,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
An
electrochemical
trifluoromethylation
method
for
terminal
alkynes
has
been
developed,
facilitating
the
synthesis
of
CF
3
-alkynes
with
DMSO
as
a
masking
auxiliary.
Язык: Английский
A Dual Catalytic Approach for the Halogen-Bonding-Mediated Reductive Cleavage of α-Bromodifluoroesters and Amides
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 19, 2024
While
charge-transfer
complexes
involving
halogen-bonding
interactions
have
emerged
as
an
alternative
strategy
for
the
photogeneration
of
carbon
radicals,
examples
using
(fluoro)alkyl
bromides
are
limited.
This
report
describes
a
dual
catalytic
approach
radical
generation
from
α-bromodifluoroesters
and
amides
under
visible-light
irradiation.
Mechanistic
studies
suggest
that
reaction
proceeds
through
in
situ
bromide
displacement
iodide
salt,
generating
C–I
bond
can
be
engaged
by
our
photocatalysis
platform.
Язык: Английский