Chinese Journal of Organic Chemistry >
Copper-Catalyzed Synthesis of β-Keto Sulfones from Enol Silyl Ether and Sodium Arylsulfinates
Received date: 2023-04-20
Revised date: 2023-06-02
Online published: 2023-06-26
Supported by
Higher Education Program in Jiangsu Province(22KJD150003); FY2023 Jiangsu Normal University Laboratory Research Project(L2023YB08)
β-Keto sulfones are an important group of sulfur-containing compounds and intermediates for organic synthesis, which are widely used in the construction of natural products and various important organic compounds. A method for the rapid synthesis of β-keto sulfones catalyzed by copper bromide from enol silyl ether and sodium arylsulfinates is developed, which has the advantages of simple operation, mild conditions and short reaction time.
Key words： β-keto sulfone; copper catalysis; enol silyl ether; sodium arylsulfinate
Li Xu , Lanlan Lü , Xiangshan Wang . Copper-Catalyzed Synthesis of β-Keto Sulfones from Enol Silyl Ether and Sodium Arylsulfinates[J]. Chinese Journal of Organic Chemistry, 2023 , 43(10) : 3644 -3651 . DOI: 10.6023/cjoc202304029
| [1] | Markitanov M.; Timoshenko V.; Shermolovich Y. J. Sulfur Chem. 2014, 35, 188. |
| [2] | Yang H.; Carter R.; Zakharov L. J. Am. Chem. Soc. 2008, 130, 9238. |
| [3] | Curti C.; Laget M.; Carle A.; Gellis A.; Vanelle P. Eur. J. Med. Chem. 2007, 42, 880. |
| [4] | Xiang J.; Ipek M.; Suri V.; Tam M.; Xing Y.; Huang N.; Zhang Y.; Tobin J.; Mansour T.; McKew J. Bioorg. Med. Chem. 2007, 15, 4396. |
| [5] | Xiang J.; Ipek M.; Suri V.; Massefski W.; Pan N.; Ge Y.; Tam M.; Xing Y.; Tobin J.; Xu X.; Tam S. Bioorg. Med. Chem. Lett. 2005, 15, 2865. |
| [6] | Peng H.; Cheng Y.; Ni N.; Li M.; Choudhary G.; Chou H.; Lu C.; Tai P.; Wang B. ChemMedChem 2009, 4, 1457. |
| [7] | Montgomery J.; Brown M.; Reilly U.; Price L.; Abramite J.; Arcari J.; Barham R.; Che Y.; Chen J.; Chung S.; Collantes E.; Desbonnet C.; Doroski M.; Doty J.; Engtrakul J.; Harris T.; Huband M.; Knafels J.; Leach K.; Liu S.; Marfat A.; McAllister L.; McElroy E.; Menard C.; Mitton-Fry M.; Mullins L.; Noe M.; O’Donnell J.; Oliver R.; Penzien J.; Plummer M.; Shanmuga- sundaram V.; Thoma C.; Tomaras A.; Uccello D.; Vaz A.; Wishka D. J. Med. Chem. 2012, 55, 1662. |
| [8] | Swenson R.; Sowin T.; Zhang H. J. Org. Chem. 2002, 67, 9182. |
| [9] | Manche?o O.; Tangen P.; Rohlmann R.; Fr?hlich R.; Alemán J. Chem.-Eur. J. 2011, 17, 984. |
| [10] | Chang M.; Cheng Y.; Lu Y. Org. Lett. 2014, 16, 6252. |
| [11] | Chang M.; Chen Y.; Chan C. Tetrahedron 2015, 71, 782. |
| [12] | Saraiva M.; Costa G.; Seus N.; Schumacher R.; Perin G.; Paix?o M.; Luque R.; Alves D. Org. Lett. 2015, 17, 6206. |
| [13] | Chang M.; Chen H.; Tsai Y. Org. Lett. 2019, 21, 1832. |
| [14] | Thomsen M.; Handwerker B.; Katz S.; Belser R. J. Org. Chem. 1988, 53, 906. |
| [15] | Katritzky A.; Abdel-Fattah A.; Wang M. J. Org. Chem. 2003, 68, 1443. |
| [16] | Suryakiran N.; Reddy T.; Ashalatha K.; Lakshman M.; Venkate- swarlu Y. Tetrahedron Lett. 2006, 47, 3853. |
| [17] | Suryakiran N.; Prabhakar P.; Rajesh K.; Suresh V.; Venkate- swarlu Y. J. Mol. Catal. A: Chem. 2007, 270, 201. |
| [18] | Trost B.; Curran D. Tetrahedron Lett. 1981, 22, 1287. |
| [19] | Cooper G.; Dolby L. Tetrahedron Lett. 1976, 17, 4675. |
| [20] | Mao R.; Yuan Z.; Li Y.; Wu J. Chem.-Eur. J. 2017, 23, 8176. |
| [21] | Liu T.; Zheng D.; Ding Y.; Fan X.; Wu J. Chem.-Asian J. 2017, 12, 465. |
| [22] | Gong X.; Ding Y.; Fan X.; Wu J. Adv. Synth. Catal. 2017, 359, 2999. |
| [23] | He F.-S.; Yao Y.; Xie W.; Wu J. Chem. Commuun. 2020, 56, 9469. |
| [24] | Ye S.; Li X.; Xie W.; Wu J. Eur. J. Org. Chem. 2020, 2020, 1274. |
| [25] | Ghosh S.; Samanta S.; Ghosh A, K.; Neogi S.; Hajra A. Adv. Synth. Catal. 2020, 362, 4552 |
| [26] | Tang X.; Huang L.; Xu Y.; Yang J.; Wu W.; Jiang H. Angew. Chem., Int. Ed. 2014, 53, 4205. |
| [27] | Tang Y.; Zhang Y.; Wang K.; Li X.; Xu X.; Du X. Org. Biomol. Chem. 2015, 13, 7084. |
| [28] | Tang Y.; Fan Y.; Gao H.; Li X.; Xu X. Tetrahedron Lett. 2015, 56, 5616. |
| [29] | Yadav V. K.; Srivastava V. P.; Yadav L. D. S. Synlett 2016, 27, 427. |
| [30] | Lu Q.; Chen J.; Liu C.; Huang Z.; Peng P.; Wang H.; Lei A. RSC Adv. 2015, 5, 24494. |
| [31] | Wang H.; Wang G.; Lu Q.; Chiang C.-W.; Peng P.; Zhou J.; Lei A. Chem.-Eur. J. 2016, 22, 14489. |
| [32] | Xu J.; Shen C.; Qin X.; Wu J.; Zhang P.; Liu X. J. Org. Chem. 2021, 86, 3706. |
| [33] | Singh A.; Chawla R.; Yadav L. Tetrahedron Lett. 2014, 55, 2845. |
| [34] | Xiong Y.; Weng J.; Lu G. Adv. Synth. Catal. 2018, 360, 1611. |
| [35] | Ning Z.; Xu Z.; Liu R.; Du Z. Synth. Commun. 2021, 51, 3492. |
| [36] | Xu J.; Shen C.; Qin X.; Wu J.; Zhang P.; Liu X. J. Org. Chem. 2021, 86, 3706. |
| [37] | Rawat V.; Reddy P.; Sreedhar B. RSC Adv. 2014, 4, 5165. |
| [38] | Xia J.; Huang X.; You S.; Cai M. Appl. Organomet. Chem. 2019, 33, e5001. |
| [39] | Cai S.; Chen D.; Xu Y.; Weng W.; Li L.; Zhang R.; Huang M. Org. Biomol. Chem. 2016, 14, 4205. |
| [40] | Kumar N.; Kumar A. ACS Sustainable Chem. Eng. 2019, 7, 9182. |
| [41] | Lin B.; Kuang J.; Chen J.; Hua Z.; Khakyzadeh V.; Xia Y. Org. Chem. Front. 2019, 6, 2647. |
| [42] | Tang Y.; Zhang Y.; Wang K.; Li X.; Xu X.; Du X. Org. Biomol. Chem. 2015, 13, 7084. |
| [43] | Katrun P.; Songsichan T.; Soorukram D.; Pohmakotr M.; Reutrakul V.; Kuhakarn C. Synthesis 2017, 49 1109. |
| [44] | Deng S.; Liang E.; Wu Y.; Tang X. Tetrahedron Lett. 2018, 59, 3955. |
| [45] | Yavari I.; Shaabanzadeh S. Org. Lett. 2020, 22, 464. |
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