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Synlett 2018; 29(09): 1232-1238
DOI: 10.1055/s-0037-1609320
DOI: 10.1055/s-0037-1609320
letter
Fe(III)/l-Valine-Catalyzed One-Pot Synthesis of N-Sulfinyl- and N-Sulfonylimines via Oxidative Cascade Reaction of Alcohols with Sulfinamides or Sulfonamides
Authors
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).
Weitere Informationen
Publikationsverlauf
Received: 26. November 2017
Accepted after revision: 29. Januar 2018
Publikationsdatum:
05. März 2018 (online)
Abstract
An efficient Fe(III), l-valine, and 4-OH-TEMPO catalytic system was found for the oxidation of alcohols followed by condensation with sulfinamide or sulfonamide in one pot for the synthesis of N-sulfinyl- and N-sulfonylimines compounds under mild conditions. This transformation accommodates a variety of substrates, shows high functional-group tolerance, and affords the corresponding products in good to excellent yields.
Key words
Fe catalysis - one-pot - N-sulfinylimines - N-sulfonylimines - oxidative cascade - alcoholsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609320.
- Supporting Information (PDF)
-
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- 19 Typical Procedure for the Synthesis of N-Sulfinylimine [(±)-N-Benzylidene-p-toluenesulfinamide]: A mixture of p-toluenesulfinamide (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 column chromatography on silica gel to give the pure product 3aa. 1H NMR (500 MHz, CDCl3): δ = 8.77 (s, 1 H), 7.82–7.90 (m, 2 H), 7.65 (d, J = 8.2 Hz, 2 H), 7.51 (t, J = 8.6 Hz, 1 H), 7.46 (t, J = 7.3 Hz, 2 H), 7.32 (d, J = 8.0 Hz, 2 H), 2.40 (s, 3 H). 13C NMR (125 MHz, CDCl3): δ = 160.67, 141.84, 141.73, 133.93, 132.59, 129.85, 129.60, 128.90, 124.82, 21.43.
- 20 Typical Procedure for the Synthesis of N-Sulfonylimine [(E)-N-Benzylidene-p-toluenesulfonamide]: A mixture of p-toluenesulfonamide (0.0685 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 flash column chromatography or purified by precipitation from CH2Cl2–pentane to give the pure product 3ea. 1H NMR (500 MHz, CDCl3): δ = 9.05 (s, 1 H), 7.93 (ddd, J = 17.4, 7.4, 1.6 Hz, 4 H), 7.60–7.67 (m, 1 H), 7.50 (t, J = 7.8 Hz, 2 H), 7.36 (d, J = 8.1 Hz, 2 H), 2.45 (s, 3 H). 13C NMR (125 MHz, CDCl3): δ = 170.13, 144.60, 134.92, 132.42, 131.30, 129.81, 129.14, 128.11, 126.48, 21.66.