F
G. Zhang et al.
Letter
Synlett
ate F obtained by the nucleophilic addition reaction, which
takes place via intramolecular hydrogen to give the species
G. Subsequently, liberation of water from G delivers the
product H along with the generation of FeCl3 for entry into
the subsequent catalytic cycles.
In conclusion, we have demonstrated a first example of
Fe-catalyzed aerobic oxidative one-pot synthesis of N-
sulfinyl and N-sulfonylimines directly from alcohols.19,20
The protocol is highly efficient and has a broad substrate
scope. Further studies to more clearly understand the reac-
tion mechanism and the synthetic applications are current-
ly underway in our laboratory.
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Funding Information
We acknowledge financial support from the National Natural Science
Foundation of China (no. 21506189), the National Natural Science
Foundation of China (no. 20702051), the Natural Science Foundation
of Zhejiang Province (LY13B020017) and the Key Innovation Team of
Science and Technology in Zhejiang Province (no. 2010R50018).
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(11) Hasaninejad, A.; Zare, A.; Sharghi, H.; Shekouhy, M. ARKIVOC
2008, (xi), 64.
Supporting information for this article is available online at
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(19) Typical Procedure for the Synthesis of N-Sulfinylimine [(±)-
N-Benzylidene-p-toluenesulfinamide]: A mixture of p-tolue-
nesulfinamide (0.0621 g, 0.4 mmol), phenylmethanol (0.0648 g,
0.6 mmol), L-valine (0.0047 g, 0.04 mmol), FeCl3 (0.0065 g,
0.04 mmol), 4-OH-TEMPO (0.0138 g, 0.08 mmol), toluene
(2.5 mL), and 4 Å MS (0.7000 g) were added to a 100-mL Schlenk
tube. Then the resulting mixture was vigorously stirred under
O2 (1 atm) at 60 °C for 24 h. After the reaction was complete, the
residue was filtered off, and the solvent was removed under
vacuum to give the crude product, which was purified by
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–G