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, Table of Contents

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

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

› Author Affiliations

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

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References

References and Notes
1 Belowich ME. Stoddart JF. Chem. Soc. Rev. 2012; 41: 2003
2 Pablo O. Collados JF. Harutyunyan SR. Eur. J. Org. Chem. 2016; 2016: 1247
3 Zhou P. Chen BC. Davis FA. Tetrahedron 2004; 60: 8003

4a Bégué JP. Bonnet-Delpon D. Crousse B. Legros J. Chem. Soc. Rev. 2005; 34: 562
4b Weinreb SM. Orr RK. Synthesis 2005; 1205
4c Senanayake CH. Krishnamurthy D. Lu ZH. Han Z. Gallou I. Aldrichimica Acta 2005; 38: 93
4d Gohain M. Synlett 2003; 2097
4e Ellman JA. Pure Appl. Chem. 2003; 75: 39
4f Ellman JA. Owens TD. Tang TP. Acc. Chem. Res. 2002; 35: 984
4g Davis FA. Zhou P. Chen BC. Chem. Soc. Rev. 1998; 27: 13
4h Bloch R. Chem. Rev. 1998; 98: 1407
4i Enders D. Reinhold U. Tetrahedron: Asymmetry 1997; 8: 1895

5a Nakamura S. Hayashi M. Hiramatsu Y. Shibata N. Funahashi Y. Toru T. J. Am. Chem. Soc. 2009; 131: 18240
5b Tan C. Liu X. Wang L. Wang J. Feng X. Org. Lett. 2008; 10: 5305
5c Hou Z. Wang J. Liu X. Feng X. Chem. Eur. J. 2008; 14: 4484
5d Ooi T. Uematsu Y. Maruoka K. J. Am. Chem. Soc. 2006; 128: 2548
5e Duan HF. Jia YX. Wang LX. Zhou QL. Org. Lett. 2006; 8: 2567
5f Fujisawa H. Takahashi E. Mukaiyama T. Chem. Eur. J. 2006; 12: 5082
5g Soeta T. Kuriyama M. Tomioka K. J. Org. Chem. 2005; 70: 297
5h Hayashi T. Kawai M. Tokunaga N. Angew. Chem. Int. Ed. 2004; 43: 6125
5i Wipf P. Kendall C. Stephenson CR. J. J. Am. Chem. Soc. 2003; 125: 761
5j Aggarwal VK. Alonso E. Ferrara M. Spey SE. J. Org. Chem. 2002; 67: 2335

6a Kwak SH. Lee SA. Lee KI. Tetrahedron: Asymmetry 2010; 21: 800
6b Yang Q. Shang G. Gao W. Deng J. Zhang X. Angew. Chem. Int. Ed. 2006; 45: 3832

7 Yamada KI. Fujihara H. Yamamoto Y. Miwa Y. Taga T. Tomioka K. Org. Lett. 2002; 4: 3509

8a Morales S. Guijarro FG. Garcia Ruano JL. Cid MB. J. Am. Chem. Soc. 2014; 136: 1082
8b Morgan PE. McCague R. Whiting A. J. Chem. Soc., Perkin Trans. 1 2000; 515
8c Yao S. Johannsen M. Hazell RG. Jørgensen KA. Angew. Chem. Int. Ed. 1998; 37: 3121
8d Bauer T. Szymański S. Jezewski A. Gluziński P. Jurczak J. Tetrahedron: Asymmetry 1997; 8: 2619
8e Sisko J. Weinreb SM. Tetrahedron Lett. 1989; 30: 3037

9a Heuer H. Smalla K. Environ. Microbiol. 2007; 9: 657
9b Wahl C. Liptay S. Adler G. Schmid RM. J. Clin. Invest. 1998; 101: 1163
9c Trube G. Rorsman P. Ohnoshosaku T. Pflugers. Arch. 1986; 407: 493
9d Moore PR. Evenson A. Luckey TD. Mccoy E. Elvehjem CA. Hart EB. J. Biol. Chem. 1946; 165: 437

10a Zolfigol MA. Tavasoli M. Moosavi-Zare AR. Arghavani-Hadi P. Zare A. Khakyzadeh V. RSC Adv. 2013; 3: 7692
10b Shintani R. Takeda M. Soh YT. Ito T. Hayashi T. Org. Lett. 2011; 13: 2977
10c Wu XF. Vovard-Le Bray C. Bechki L. Darcel C. Tetrahedron 2009; 65: 7380
10d García Ruano JL. Alemán J. Cid MB. Parra A. Org. Lett. 2005; 7: 179
10e Wynne JH. Price SE. Rorer JR. Stalick WM. Synth. Commun. 2003; 33: 341
10f Ram RN. Khan AA. Synth. Commun. 2001; 31: 841
10g Artman Iii GD. Bartolozzi A. Franck RW. Weinreb SM. Synlett 2001; 232
10h Boger DL. Corbett WL. Curran TT. Kasper AM. J. Am. Chem. Soc. 1991; 113: 1713
10i Jennings WB. Lovely CJ. Tetrahedron Lett. 1988; 29: 3725

11 Hasaninejad A. Zare A. Sharghi H. Shekouhy M. ARKIVOC 2008; (xi): 64

12a Moreau P. Essiz M. Mérour JY. Bouzard D. Tetrahedron: Asymmetry 1997; 8: 591
12b Liu G. Cogan DA. Ellman JA. J. Am. Chem. Soc. 1997; 119: 9913
12c Yang TK. Chen RY. Lee DS. Peng WS. Jiang YZ. Mi AQ. Jong TT. J. Org. Chem. 1994; 59: 914
12d Davis FA. Reddy RE. Szewczyk JM. Portonovo PS. Tetrahedron Lett. 1993; 34: 6229
12e Hua DH. Miao SW. Chen JS. Iguchi S. J. Org. Chem. 1991; 56: 4
12f Annunziata R. Cinquini M. Cozzi F. Raimondi L. Gazz. Chim. Ital. 1989; 119: 253

13a Phillips F. Martins AM. M. Pombeiro A. Kopylovich M. ChemCatChem 2016; 9: 217
13b Barta K. Ford PC. Acc. Chem. Res. 2014; 47: 1503

14a Zhang G. Lei J. Han X. Luan Y. Ding C. Shan S. Synlett 2015; 26: 779
14b Zhang G. Han X. Luan Y. Wang Y. Wen X. Xu L. Ding C. Gao J. RSC Adv. 2013; 3: 19255
14c Zhang G. Han X. Luan Y. Wang Y. Wen X. Ding C. Chem. Commun. 2013; 49: 7908

15 Patel R. Srivastava VP. Yadav LD. S. Adv. Synth. Catal. 2010; 352: 1610
16 Zhang G. Xu S. Xie X. Ding C. Shan S. RSC Adv. 2017; 7: 9431
17 Zhang G. Li S. Lei J. Zhang G. Xie X. Ding C. Liu R. Synlett 2016; 27: 956
18 Dijksman A. Arends IW. C. E. Sheldon RA. Org. Bio. Chem. 2003; 1: 3232
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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