Fe(III)/l-Valine-Catalyzed One-Pot Synthesis of N-Sulfinyl- and N-Sulfonylimines via Oxidative Cascade Reaction of Alcohols with Sulfinamides or Sulfonamides

Guofu Zhang; Yunzhe Xing; Shengjun Xu; Chengrong Ding; Shang Shan

doi:10.1055/s-0037-1609320

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(09): 1232-1238
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

Autor*innen

Guofu Zhang

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China eMail: dingcr@zjut.edu.cn eMail: shans2001@163.com
Yunzhe Xing

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China eMail: dingcr@zjut.edu.cn eMail: shans2001@163.com
Shengjun Xu

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China eMail: dingcr@zjut.edu.cn eMail: shans2001@163.com
Chengrong Ding*

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China eMail: dingcr@zjut.edu.cn eMail: shans2001@163.com
Shang Shan*

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China eMail: dingcr@zjut.edu.cn eMail: shans2001@163.com

Abstract

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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 - alcohols

Volltext

Referenzen

References and Notes
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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.

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