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Organic & Biomolecular Chemistry
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Journal Name
ARTICLE
Radical inhibiting experiment
Schwan, J. Org. Chem., 2012, 77, 10978.
DOI: 10.1039/C9OB00864K
SO2Na
N2BF4
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Chem., 2016, 16, 1200.
eosin Y (1 mol%)
O
O
S
N
O
MeCN/H2O (10: 1 )
green LEDs, N2, rt
TEMPO (3 equiv.)
NC
3j
5
CN
traces
6
CN
Radical trapping experiment
O
S
O
N2BF4
SO2Na
6 (a) N.-W. Liu, S. Liang and G. Manolikakes, Synthesis, 2016, 48,
1939; (b) S. Shaaban, S. Liang, N.-W. Liu and G. Manolikakes, Org.
Biomol. Chem., 2017, 15, 1947.
eosin Y (1 mol%)
NC
CN
3j
MeCN/H2O (10: 1 )
green LEDs, N2, rt
Ts
CN
7 For recent examples, see: (a) G. Le Duc, E. Bernoud, G. Prestat, S.
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7
8
Scheme 2 Mechanistic investigations.
Conclusions
In summary, we have developed a transition-metal- and
external oxidant/reductant-free visible-light-mediated approach for
the synthesis of diaryl/alkyl aryl sulfones from aryl diazonium and
sulfinate salts employing eosin Y as an organophotoredox catalyst
under mild conditions. The protocol is operationally very simple and
utilizes visible light as an inexpensive and ecosustainable energy
source in aqueous acetonitrile as an acceptable green solvent at
ambient temperature. The developed method overcomes a number
of limitations of the previously reported methods and qualifies well
as an applaudable entry in the arena of green synthetic methods for
the procurement of sulfones. Moreover, the desired diaryl/alkyl aryl
sulfones were also synthesized by a one-pot, two-step process
involving an in situ diazotization of a number of anilines followed by
VLPC enabled arylation of sulfinate salts.
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Conflicts of interest
“There are no conflicts to declare”.
Acknowledgements
We sincerely thank SAIF, Punjab University, Chandigarh, for
providing microanalyses and spectra.
Notes and references
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