Subscribe to RSS
DOI: 10.1055/a-2530-4542
Synthesis of N-Containing Halogenated Synthons by Surfactant-Mediated Direct Vicinal Difunctionalization of Alkenes in Aqueous Medium
University of Calcutta.

Abstract
In an aqueous medium, this metal-free and benign strategy enables direct installation of C–N and C–X bonds into olefins using the organic Lewis acid, PhIO. The surfactant-mediated vicinal difunctionalization enables the synthesis of N-tosyl-1,2-bromoamines and 1,2-bromoazides with good regio- and stereoselectivity. This strategy provides a straightforward route to sugar-based chiral and functionally diverse synthons that hold great promise for applications in pharmaceutical chemistry.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2530-4542.
- Supporting Information
Publication History
Received: 30 November 2024
Accepted after revision: 31 January 2025
Accepted Manuscript online:
31 January 2025
Article published online:
19 March 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References and Notes
- 1a Zheng Y, Lu W, Chen C, Lu Y, Huang S. Org. Chem. Front. 2024; 11: 5306
- 1b Yan-mei L, Jin-feng F, Long-qiang H, Wei-na L, Vessally E. RSC Adv. 2021; 11: 24474
- 1c Jensen KH, Webb JD, Sigman MS. J. Am. Chem. Soc. 2010; 132: 17471
- 2a Wickham LM, Giri R. Chem. Res. 2021; 54: 3415
- 2b Oh SH, Malpani YR, Ha N, Jung Y. -S, Han SB. Org. Lett. 2014; 16: 1310
- 2c Jesus M, Afonso C, Sookezian A, Badir SO, Khatib ME, Molander GA. Chem. Sci. 2021; 12: 9189
- 2d Dong B, Shen J, Xie LG. Org. Chem. Front. 2023; 10: 1322
- 2e Harper MJ, Emmett EJ, Bower JF, Russell CA. J. Am. Chem. Soc. 2017; 139: 12386
- 2f Willis MC. Chem. Rev. 2010; 110: 725
- 3a Béke F, Mészáros Á, Tóth Á, Botlik BB, Novák Z. Nat. Commun. 2020; 11: 5924
- 3b Pandit P, Gayen KS, Khamarui S, Chatterjee N, Maiti DK. Chem. Commun. 2011; 47: 6933
- 3c Ghosh D, Ganguly A, Khamarui S. Org. Biomol. Chem. 2023; 21: 5225
- 3d Chan A, Scheidt KA. J. Am. Chem. Soc. 2007; 129: 5334
- 3e Wei Y, Shi M. Acc. Chem. Res. 2010; 43: 1005
- 3f Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
- 4 Yeung YY, Gao X, Corey EJ. J. Am. Chem. Soc. 2006; 128: 9644
- 5 Boyer JH. J. Am. Chem. Soc. 1951; 73: 5865
- 6 Cantillo D, Gutmanna B, Kappe CO. Org. Biomol. Chem. 2016; 14: 853
- 7a Huisgen R. Angew. Chem., Int. Ed. Engl. 1963; 2: 565
- 7b Tornøe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
- 7c Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 7d Amantini D, Fringuelli F, Piermatti O, Pizzo F, Zunino E, Vaccaro L. J. Org. Chem. 2005; 70: 6526
- 8a Wei J.-f, Zhang L.-h, Chen Z.-g, Shi X.-y, Cao J.-j. Org. Biomol. Chem. 2009; 7: 3280
- 8b Wei J.-F, Chen Z.-G, Lei W, Zhang L.-H, Wang M.-Z, Shi X.-Y, Li R.-T. Org. Lett. 2009; 11: 4216
- 8c Wu X.-L, Wang G.-W. Tetrahedron 2009; 65: 8802
- 8d Wu X.-L, Wang G.-W. Eur. J. Org. Chem. 2008; 6239
- 9a Li G, Wei H.-X, Kim SH, Neighbors M. Org. Lett. 1999; 1: 395
- 9b Thakur VV, Talluri SK, Sudalai A. Org. Lett. 2003; 5: 861
- 9c Shaikh TM, Karabal PU, Suryavanshi G, Sudalai A. Tetrahedron Lett. 2009; 50: 2815
- 10 Xu X, Kotti SR. S. S, Liu J, Cannon JF, Headley AD, Li G. Org. Lett. 2004; 6: 4881
- 11 Wu X.-L, Wang G.-W. J. Org. Chem. 2007; 72: 9398
- 12a Kharasch MS, Priestley HM. J. Am. Chem. Soc. 1939; 61: 3425
- 12b Ueno Y, Takemura S, Ando Y, Terauchi H. Chem. Pharm. Bull. 1967; 15: 1193
- 12c Xia J.-J, Wu X.-L, Wang GW. ARKIVOC 2008; (xvi): 22
- 13a Klepacz A, Zwierzak A. Tetrahedron Lett. 2001; 42: 4539
- 13b Sliwinska A, Zwierzak A. Tetrahedron Lett. 2003; 44: 9323
- 13c Sliwinska A, Zwierzak A. Tetrahedron 2003; 59: 5927
- 14a Lessard J, Driguez H, Vermes J.-P. Tetrahedron Lett. 1970; 4887
- 14b Driguez H, Vermes J.-P, Lessard J. Can. J. Chem. 1978; 56: 119
- 15a Hajra S, Sinha D, Bhowmick M. Tetrahedron Lett. 2006; 47: 7017
- 15b Hajra S, Sinha D, Bhowmick M. J. Org. Chem. 2007; 72: 1852
- 15c Ende DV, Krief A. Angew. Chem. Int. Ed. Engl. 1974; 13: 279
- 15d Denis JN, Krief A. Tetrahedron 1979; 35: 2901
- 15e Olah GO, Wang Q, Li X.-Y, Prakash GK. S. Synlett 1990; 487
- 16a Hassner A, Boerwinkle F. J. Am. Chem. Soc. 1968; 90: 216
- 16b Boerwinkle F, Hassner A. Tetrahedron Lett. 1968; 3921
- 16c Hassner A, Boerwinkle F. Tetrahedron Lett. 1969; 3309
- 16d Fowler FW, Hassner A, Levy LA. J. Am. Chem. Soc. 1967; 89: 2077
- 16e Hassner A, Fowler FW. J. Org. Chem. 1968; 33: 2686
- 17 Fu J, Zanoni G, Anderson EA, Bi X. Chem. Soc. Rev. 2017; 46: 7208
- 18 Saikia I, Phukan P. Tetrahedron Lett. 2009; 50: 5083
- 19a Nair V, George TG, Sheeba V, Augustine A, Balagopal L, Nair LG. Synlett 2000; 1597
- 19b Curini M, Epifano F, Marcotullio MC, Rosati O. Tetrahedron Lett. 2002; 43: 1201
- 20a Schulz G, George V, Taser D, Kirschning A. J. Org. Chem. 2023; 88: 3781
- 20b Barluenga J, Alvarez-Perez M, Fananas FJ, Gonzales JM. Adv. Synth. Catal. 2001; 343: 335
- 21 Wu X.-L, Xia J.-J, Wang G.-W. Org. Biomol. Chem. 2008; 6: 548
- 22 Kirschning A, Hashem MdA, Monenschein H, Rose L, Schöning K.-U. J. Org. Chem. 1999; 64: 6523