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Synthesis 2024; 56(12): 1941-1957
DOI: 10.1055/a-2259-5395
DOI: 10.1055/a-2259-5395
paper
Phosphazene-Catalyzed Regioselective Condensation of Allyl Thioethers with Aldehydes: A Rapid Approach to 1,3-Dienyl Sulfides, -Sulfoxides and -Sulfones
This project is funded by the National Research Council of Thailand (NRCT) and Mahidol University (N42A650346) and the Thailand Toray Science Foundation (TTSF). A student scholarship to S.P. from the National Science and Technology Development Agency (NSTDA) and Nakhon Ratchasima Rajabhat University (NRRU) are gratefully acknowledged.
Abstract
The phosphazene-catalyzed regioselective condensation of allyl thioethers with aldehydes is investigated. Upon treatment of allyl thioethers with P4-t-Bu, allyl thioether anions are generated and rapidly react with aromatic aldehydes, leading to 1,3-dienyl sulfides in good yields with high regioselectivity. This finding provides an alternative approach for the preparation of allyl thioether anions in a regioselective manner. In addition, chemoselective transformations of 1,3-dienyl sulfides to provide the corresponding 1,3-dienyl sulfoxides or 1,3-dienyl sulfones are also demonstrated.
Key words
1,3-dienyl sulfides - 1,3-dienyl sulfones - 1,3-dienyl sulfoxides - phosphazene - allyl thioethers - allyl sulfides - organosulfurSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2259-5395.
- Supporting Information
Publication History
Received: 09 January 2024
Accepted after revision: 01 February 2024
Accepted Manuscript online:
01 February 2024
Article published online:
27 February 2024
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References
- 1 Katritzky AR, Piffl M, Lang H, Anders E. Chem. Rev. 1999; 99: 665
- 2a Piffl M, Weston J, Günther W, Anders E. J. Org. Chem. 2000; 65: 5942
- 2b Gerhards F, Griebel N, Runsink J, Raabe G, Gais H.-J. Chem. Eur. J. 2015; 21: 17904
- 2c Li X, Lantrip D, Fuchs PL. J. Am. Chem. Soc. 2003; 125: 14262
- 3 Schwesinger R, Schlemper H. Angew. Chem., Int. Ed. Engl. 1987; 26: 1167 ; Angew. Chem., 1987, 99, 1212
- 4a Punirun T, Soorukram D, Kuhakarn C, Reutrakul V, Pohmakotr M. Eur. J. Org. Chem. 2014; 4162
- 4b Racochote S, Naweephattana P, Surawatanawong P, Kuhakarn C, Leowanawat P, Reutrakul V, Soorukram D. Org. Biomol. Chem. 2023; 21: 7180
- 4c Luo C, Bandar JS. J. Am. Chem. Soc. 2018; 140: 3547
- 4d Kondoh A, Yamaguchi S, Watanabe Y, Terada M. Synlett 2022; 33: 1853
- 5a Cornil J, Guérinot A, Cossy J. Org. Biomol. Chem. 2015; 13: 4129
- 5b Velado M, Martinović M, Alonso I, Tortosa M, de la Pradilla RF, Viso A. J. Org. Chem. 2023; 88: 3697
- 5c Kong W, Che C, Kong L, Zhu G. Tetrahedron Lett. 2015; 56: 2780
- 5d Cai M.-Z, Wang D, Wang P.-P. J. Organomet. Chem. 2006; 691: 737
- 5e Cai M.-Z, Chen G.-Q, Hao W.-Y, Wang D. J. Organomet. Chem. 2007; 692: 1125
- 5f Yao F, Hao W, Cai M. J. Chem. Res. 2009; 558
- 5g Aversa MC, Barattucci A, Banaccorsi P, Giannetto P. Tetrahedron: Asymmetry 1997; 8: 1339
- 5h Zhang T, Wang R, Chen J, Liu L, Huang T, Li C, Tang Z, Chen T. Org. Biomol. Chem. 2022; 20: 4369
- 5i Britten TK, Basson AJ, Roberts DD, McLaughlin MG. Synthesis 2021; 53: 3535
- 5j Everhardus RH, Gräfing R, Brandsma L. Synthesis 1983; 8: 623
- 6a Gao P, Zhang Q, Chen F. Org. Lett. 2022; 24: 7769
- 6b Nakabayashi K, Abiko Y, Mori H. Macromolecules 2013; 46: 5998
- 6c Kausar A, Zulfiqar S, Sarwar MI. Polym. Rev. 2014; 54: 185
- 6d Everhardus RH, Gräfing R, Brandsma L. Recl. Trav. Chim. Pays-Bas 1978; 97: 69
- 6e Paz-Michel BA, González-Bravo FJ, Hernández-Muñoz LS, Guzei IA, Paz-Sandoval MA. Organometallics 2010; 29: 3694
- 6f Gamero-Melo P, Melo-Trejo PA, Cervantes-Vasquez M, Mendizabal-Navarro NP, Paz-Michel B, Villar-Masetto TI, Gonzalez-Fuentes MA, Paz-Sandoval MA. Organometallics 2012; 31: 170
- 6g Geiger VJ, Oechsner RM, Gehrtz PH, Fleischer I. Synthesis 2022; 54: 5139
- 7a Liu C, Xu J, Wu G. RSC Adv. 2021; 11: 35156
- 7b Dong J, Xu J. Synthesis 2018; 50: 2407
- 7c Sahharova LT, Gordeev EG, Eremin DB, Ananikov VP. ACS Catal. 2020; 10: 9872
- 8a Pal P, Fragis M, Dharavath S, Johnson JW, Magolan J. Synthesis 2022; 54: 4917
- 8b Fragis M, Deobald JL, Dharawath S, Scott J, Magolan J. Org. Lett. 2021; 23: 4548
- 9 Bachmann DG, Wittwer CC, Gillingham DG. Adv. Synth. Catal. 2013; 355: 3703
- 10 Jones SB, Simmons B, MacMillan DW. C. J. Am. Chem. Soc. 2009; 131: 13606 ; see also Ref. 5
- 11 Wu W, Verkade JG. ARKIVOC 2004; (ix): 88
- 12 See the Supporting Information for the assignment of the (1E,3E) and (1Z,3E) isomers.
- 13 It was found that 4a is thermally unstable and decomposes gradually (1H NMR analysis) upon storage either at room temperature (35 °C) or at 0 °C, whereas 5a is more stable and can be kept at 0 °C.
- 14 Xu X, Yan L, Wang S, Wang P, Yang A.-X, Li X, Lu H, Cao Z. Org. Biomol. Chem. 2021; 19: 8691
- 15 The α-regioselectivity was confirmed based on the structure elucidation of 5d by 2D NMR experiments, see the Supporting Information.
- 16 Daines RA, Chambers PA, Pendrak I, Jakas DR, Sarau HM, Foley JJ, Schmidt DB, Kingsbury WD. J. Med. Chem. 1993; 36: 3321
- 17a Arribas C, Carreño CC, García-Ruano JL, Rodríguez JF, Santos M, Sanz-Tejedor A. Org. Lett. 2000; 2: 3165
- 17b Kalyanakrishnan AV, Joshy A, Arya AK, Kaliyamoorthy A. ChemistrySelect 2021; 6: 14054
- 17c de la Pradilla RF, Castellanos A, Ureña M, Viso A. Phosphorus, Sulfur Silicon Relat. Elem. 2005; 180: 1461
- 17d de la Pradilla RF, Castellanos A, Osante I, Colomer I, Sánchez MI. J. Org. Chem. 2009; 74: 170
- 18a Chen Y, Zhu K, Huang Q, Lu Y. Chem. Sci. 2021; 12: 13564
- 18b Zhao H, Yang W, Xie S, Cai M. Eur. J. Org. Chem. 2012; 831
- 18c Dana D, Davalos AR, Subramaniam G, Afzal N, Hersh WH, Kumar S. Tetrahedron Lett. 2013; 54: 2717
- 19a Yamazaki M, Guha SK, Ukaji Y, Inomata K. Bull. Chem. Soc. Jpn. 2008; 81: 740
- 19b Back TG, Clary KN, Gao D. Chem. Rev. 2010; 110: 4498
- 19c Chu X.-Q, Ge D, Cui Y.-Y, Shen Z.-L, Li C.-J. Chem. Rev. 2021; 121: 12548
- 19d Hampton CS, Harmata M. Tetrahedron Lett. 2017; 58: 2530
- 20a Khaikate O, Pewklang T, Khrootkaew T, Chansaenpak K, Muangsopa P, Kuhakarn C, Kamkaew A. RSC Adv. 2023; 13: 16671
- 20b Vorasin O, Momphanao K, Katrun P, Kuhakarn C, Jiarpinitnun C. Bioorg. Med. Chem. Lett. 2022; 63: 128652
- 20c Ahmadi R, Emami S. Eur. J. Med. Chem. 2022; 234: 114255
- 20d Katrun P, Chiampanichayakul S, Korworapan K, Pohmakotr M, Reutrakul V, Jaipetch T, Kuhakarn C. Eur. J. Org. Chem. 2010; 5633
- 20e Wang M, Jiang X. ACS Sustainable Chem. Eng. 2022; 10: 671
- 21 Hurd CD, Greengard H. J. Am. Chem. Soc. 1930; 52: 3356
- 22a Posner GH, Tang P-W. J. Org. Chem. 1978; 43: 4131
- 22b Kokin K, Tsuboi S, Motoyoshiya J, Hayashi S. Synthesis 1996; 637
- 23 Zhang Z, Zhang D, Zhu L, Zeng D, Kambe N, Qiu R. Org. Lett. 2021; 23: 5317
For examples, see: