Room Temperature, Metal-Free, Regioselective Arylselenation of Anilines Using Diselenides as Selenium Source

Rekha Bai; Kamlesh Kumar Dabaria; Satpal Singh Badsara

doi:10.1055/a-1730-8186

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(10): 2487-2493
DOI: 10.1055/a-1730-8186

paper

Room Temperature, Metal-Free, Regioselective Arylselenation of Anilines Using Diselenides as Selenium Source

Rekha Bai‡

,

Kamlesh Kumar Dabaria‡

,

Satpal Singh Badsara ∗

Abstract

Alle Artikel dieser Rubrik

This work is dedicated to Professor Deevi Basavaiah (University of Hyderabad) on his 71st birthday.

Abstract

A metal-free direct C–H selenation of aniline derivatives via an iodine-catalyzed C–Se bond formation using diselenides as a selenium source at ambient temperature is described. A variety of aniline derivatives underwent regioselective C–H selenation with different diselenides to afford the corresponding aryl selenoethers in good to excellent yields.

Key words

C–H selenation - aniline derivatives - aryl selenoethers - regioselective - metal-free

Volltext

Referenzen

References

1a Sun C.-L, Shi Z.-J. Chem. Rev. 2014; 114: 9219
1b Mehta VP, Punji B. RSC Adv. 2013; 3: 11957
1c Liu W, Li J, Querard P, Li C.-J. J. Am. Chem. Soc. 2019; 141. 6755

2a Wang H, Gao X, Lv Z, Abdelilah T, Lei A. Chem. Rev. 2019; 119: 6769
2b Guo W, Tao K, Tan W, Zhao M, Zheng L, Fan X. Org. Chem. Front. 2019; 6: 2048
2c Sauermann N, Meyer TH, Tian C, Ackermann L. J. Am. Chem. Soc. 2017; 139: 18452
2d Ackermann L. Acc. Chem. Res. 2020; 53: 84
2e Yan M, Kawamata Y, Baran PS. Chem. Rev. 2017; 117: 13230
2f Yoshida J.-i, Shimizu A, Hayashi R. Chem. Rev. 2018; 118: 4702

3a Shamberger RJ. Biochemistry of Selenium . Plenum Press; New York: 1983
3b Klayman DL, Gunter WH. H. Organoselenium Compounds: Their Chemistry and Biology . Wiley-Interscience; New York: 1973
3c Rotruck JT, Pope AL, Ganther HE, Swanson AB, Hafeman DG, Hoekstra WG. Science 1973; 179: 588
3d Nogueira CW, Zeni G, Rocha JB. T. Chem. Rev. 2004; 104: 6255
3e Mugesh G, du Mont WW, Sies H. Chem. Rev. 2001; 101: 2125
3f Mugesh G, Singh HB. Chem. Soc. Rev. 2000; 29: 347

4a Braga AL, Vargas F, Sehnem JA, Braga RC. J. Org. Chem. 2005; 70: 9021
4b Schwab RS, Soares LC, Dornelles L, Rodrigues OE. D, Paixao MW, Godoi M, Braga AL. Eur. J. Org. Chem. 2010; 3574

5a Wirth T. Tetrahedron 1999; 55: 1
5b Wirth T. Angew. Chem. Int. Ed. 2000; 39: 3740
5c Godoi M, Paixao MW, Braga AL. Dalton Trans. 2011; 40: 11347

6 Perin G, Lenardao EJ, Jacob RG, Panatieri RB. Chem. Rev. 2009; 109: 1277

7a Topics in Current Chemistry in Organoselenium Chemistry. Wirth T. Springer; Heidelberg: 2000: 208
7b Krief A. In Comprehensive Organometallic Chemistry II, Vol. 11. Abel EV, Stone FG. A, Wilkinson G. Pergamon Press; New York: 1995: 515
7c Paulmier C. Selenium Reagents and Intermediates in Organic Synthesis, Organic Chemistry Series 4. Baldwin JE. Pergamon Press; Oxford: 1986

8 Freudendahl DM, Iwaoka M, Wirth T. Eur. J. Org. Chem. 2010; 3934

9a Keck GE, Grier MC. Synlett 1999; 1657
9b Chen C, Crich D, Papadatos A. J. Am. Chem. Soc. 1992; 114: 8313
9c Boger DL, Mathvink RJ. J. Org. Chem. 1992; 57: 1429
9d Hiiro T, Morita Y, Inoue T, Kambe N, Ogawa A, Ryuand I, Sonoda N. J. Am. Chem. Soc. 1990; 112: 455

10 Yamada J.-i, Akutsu H, Nishikawa H, Kikuchi K. Chem. Rev. 2004; 104: 5057
11 Inoue M, Yamahita S, Ishihara Y, Hirama M. Org. Lett. 2006; 8: 5805

12a Kundu D. RSC Adv. 2021; 11: 6682
12b Rodrigues J, Saba S, Joussef AC, Rafique J, Braga AL. Asian J. Org. Chem. 2018; 7: 1819
12c Kumaraswamy G, Ramesh V, Gangadhar M, Vijaykumar S. Asian J. Org. Chem. 2018; 7: 1689

13 Ricordi VG, Thurow S, Penteado F, Schumacher RF, Perin G, Lenardão EJ, Alves D. Adv. Synth. Catal. 2015; 357: 933
14 Fang X.-L, Tanga R.-Y, Zhang X.-G, Li J.-H. Synthesis 2011; 1099
15 Saba S, Rafique J, Braga AL. Catal. Sci. Technol. 2016; 6: 3087
16 Thurow S, Penteado F, Perin G, Jacob RG, Alves D, Lenardão EJ. Green Chem. 2014; 16: 3854
17 Kundu D, Ahammed S, Ranu BC. Org. Lett. 2014; 16: 1814
18 Shieh Y.-C, Du K, Basha RS, Xue Y.-J, Shih B.-H, Li L, Lee C.-F. J. Org. Chem. 2019; 84: 6223
19 Ren Y, Xu B, Zhong Z, Pittman CU. Jr, Zhou A. Org. Chem. Front. 2019; 6: 2023
20 Zhou Z, He X. Synth. Commun. 2018; 48: 2553

21a Choudhary R, Singh P, Bai R, Sharma MC, Badsara SS. Org. Biomol. Chem. 2019; 17: 9757
21b Badsara SS, Singh P, Choudhary R, Bai R, Sharma MC. New J. Chem. 2019; 43: 11045
21c Choudhary R, Bai R, Singh P, Sharma MC, Badsara SS. SynOpen 2018; 2: 213
21d Bai R, Choudhary R, Singh P, Thakuria R, Sharma MC, Badsara SS. ChemistrySelect 2018; 3: 3221
21e Singh P, Bai R, Choudhary R, Sharma MC, Badsara SS. RSC Adv. 2017; 7: 30594
21f Choudhary R, Bai R, Singh P, Sharma MC, Badsara SS. Tetrahedron 2017; 73: 4323

22a Zhang S, Koe A, Heintz C, Senior A, Jin J. Tetrahedron Lett. 2016; 57: 260
22b Rodrigues J, Saba S, Joussef AC, Rafique J, Braga AL. Asian J. Org. Chem. 2018; 7: 1819

Zusatzmaterial

Supporting Information