10.1002/asia.201801211
Chemistry - An Asian Journal
COMMUNICATION
Conflict of interest
hv
[Ru(bpy)3]2+*
-
N2+BF4
The authors declare no conflict of interest.
[Ru(bpy)3]2+
1
Keywords: photoredox catalyst, bifunctionalization, visible light,
olefins
[Ru(bpy)3]3+
1'
[1]
[2]
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A
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Ar
Ar
Ar
II
I
2
-
N2+BF4
B
[3]
1
chain
mechanism
1'
Ar
ROH
OR
3
[4]
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Scheme 3. Plausible reaction mechanism; (A) photo catalytic mechanism. (B)
radical chain mechanism.
In conclusion, we developed
a simple and versatile
photoredox-catalyzed aryl alkoxylation of styrenes. Additionally,
the developed method allows access to a variety of products
under mild reaction conditions, with a low catalyst loading and a
short reaction time. This photoredox-catalyzed aryl alkoxylation is
currently being further developed in our laboratory.
[5]
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Experimental Section
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General Procedure for aryl alkoxylation of olefins
A Pyrex® test tube (16.5 cm × 1.5 cm) containing a mixture of
diazonium salt 1 (0.3 mmol), solution of Ru(bpy)3Cl2•6H2O
dissolved in MeOH (0.05 equiv, 1.5 × 10-6 mmol) and styrene 2
(2.0 equiv, 0.6 mmol) in mixture of MeOH (1.0 mL) and MeCN
(1.0mL) was degassed via FPT cycling for three times and
backfilled with Ar. The tube was placed ca. 0.5 cm from 3 W LED.
The resulting solution was stirred at ambient temperature for 1 h.
The residue was filtrated through silica gel, washed with CHCl3,
concentrated in vacuo. The resulting mixture was purified by flash
column chromatography on silica gel (n-hexane : EtOAc = 40 : 1)
to give product 3.
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Acknowledgements
This work was supported by a JSPS KAKENHI Grant Number
JP18K14871.
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359, 3883.
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