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COMMUNICATION
Journal Name
Scheme 5: Proposed mechanism of α-sulfonylation
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In summary, a new α-sulfonylation reaction of secondary
aldehydes has been achieved using earth abundant copper catalysis.
Manganese(IV) oxide was an effective oxidant when using AcOH to
enhance the redox potential. These conditions were compatible with
the potentially sensitive aldehyde products and a wide range of
sulfinate salts. Control and radical trapping experiments indicate this
process could proceed by concurrent polar and radical mechanisms.
The utility of these aldehyde building blocks was shown by their
derivatisation into functionally diverse fragments, suggesting this
methodology may of value in medicinal chemistry programs.
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Conflicts of interest
There are no conflicts to declare.
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10 Y. A. Konik, G. Z. Elek, S. Kaabel, I. Järving, M. Lopp and D. G.
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13 For pourbaix diagram of Manganese see: a) O. V. Boytsova, T.
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Acknowledgements
We gratefully acknowledge The Royal Society for funding
[University Research Fellowship, UF140161 (to J.A.B), URF
appointed grant RG150444 and URF enhancement grant
RGF\EA\180031]
Notes and references
1
For reviews on oxidative couplings, see: (a) I. Funes-Ardoiz
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14 Only trace product was observed under silver mediated
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15 Procedure adapted from: K. Bahrami, M. M. Khodaei and F.
Naali, J. Org. Chem., 2008, 73, 6835–6837.
16 Procedure for Pictet–Spengler reaction using tertiary
aldehydes adapted from: Z. Zhao, Y. Sun, L. Wang, X. Chen, Y.
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4 | J. Name., 2012, 00, 1-3
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