硅醚与硫(VI)氟化合物SuFEx点击反应进展

doi:10.6023/cjoc202304026

摘要/Abstract

SuFEx点击反应自2014年被提出以后取得了快速的进展, 分别从小分子制备与聚合物合成方面介绍硅醚与有机硫(VI)氟化合物之间的点击化学反应, 对目前发展的硅醚与硫(Ⅵ)氟化合物SuFEx典型点击反应重点按照底物类型进行了梳理, 探讨了未来的研究方向.

关键词: 点击化学, SuFEx点击反应, 硅醚, 硫(VI)氟化合物

The last decade has witnessed the great development of SuFEx reactions. The synthetic value of SuFEx reactions in the preparation of small molecules and polymers is reviewed. The paper is arranged based on the types of substrates and the possible direction of the reaction is discussed.

Key words: click chemistry, SuFEx reaction, silyl ether, sulfur(Ⅵ) fluoride compounds

引用此文

张豪, 赵庆彬, 阮忠睿, 刘振兴. 硅醚与硫(VI)氟化合物SuFEx点击反应进展[J]. 有机化学, 2023, 43(10): 3569-3579.

Hao Zhang, Qingbin Zhao, Zhongrui Ruan, Zhenxing Liu. Recent Development of SuFEx Reaction between Silyl Ethers and Sulfur(VI) Fluoride Compounds[J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3569-3579.

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图/表 21

图式1. 早期烷基硅醚与苯磺酰氟的反应

Scheme 1. Early reports on the reaction of alkoxy trimethyl silanes and benzenesulfonates

图式2. DBU催化烷基硅醚与对甲苯磺酰氟的反应

Scheme 2. DBU-catalyzed reaction of alkyl silyl ethers and p-toluenesulfonyl fluoride

图式3. DBU催化芳基硅醚与对甲苯磺酰氟的反应

Scheme 3. DBU-catalyzed reaction of aryl silyl ethers and p-toluenesulfonyl fluoride

图式4. DBU催化芳基硅醚与β-芳基烯基磺酰氟的反应

Scheme 4. DBU-catalyzed reaction of aryl silyl ethers and β-arylethenesulfonyl fluorides

图式5. DBU催化芳基硅醚与官能团化磺酰氟的反应

Scheme 5. DBU-catalyzed reaction of aryl silyl ethers and functional sulfonyl fluorides

图式6. (nBu)4NHF2催化芳基硅醚与三氮唑磺酰氟的反应

Scheme 6. (nBu)4NHF2-catalyzed reaction of aryl silyl ethers and triazolyl sulfonyl fluorides

图式7. (Et)4NF催化的烯基硅醚与三氮唑磺酰氟的反应

Scheme 7. (Et)4NF-catalyzed reaction of alkenyl silyl ethers and triazolyl sulfonyl fluorides

图式8. NHC催化烯基硅醚与烯基磺酰氟的(3＋3)环化反应

Scheme 8. NHC-catalyzed [3＋3] annulation of alkenyl silyl ethers and alkenyl sulfonyl fluorides

图式9. DBU催化芳基硅醚与芳基氟磺酸酯的反应

Scheme 9. DBU-catalyzed reaction of aryl silyl ethers and aryl fluorosulfates

图式10. DBU或TBD催化糖基硅醚与芳基氟磺酸酯的反应

Scheme 10. DBU or TBD-catalyzed reaction of glycosyl silyl ethers and aryl fluorosulfates

图式11. DBU催化芳基硅醚与亚胺基磺酰双氟的反应

Scheme 11. DBU-catalyzed reaction of aryl silyl ethers and iminosulfur oxydifluorides

图式12. DBU催化芳基硅醚与亚胺基磺酰单氟的反应

Scheme 12. DBU-catalyzed reaction of aryl silyl ethers and sulfonimidoyl fluorides

图式13. DBU催化聚硫酸酯、聚磺酸酯类高分子合成

Scheme 13. DBU-catalyzed synthesis of polysulfates and polysulfonates

图式14. (Me2N)3S＋[FHF]-催化聚硫酸酯、聚磺酸酯类高分子合成

Scheme 14. (Me2N)3S＋[FHF]--catalyzed synthesis of polysulfates and polysulfonates

图式15. [Ph3P=NPPh3]＋[FHF]-催化聚磺酸酯类高分子合成

Scheme 15. [Ph3P=NPPh3]＋[FHF]--catalyzed synthesis of polysulfonates

图式16. DBU催化聚亚胺基磺酸酯类高分子合成

Scheme 16. DBU-catalyzed synthesis of polysulfluoridoimidiate

图式17. SuFEx点击反应与活性自由基聚合反应协同使用制备聚合物

Scheme 17. Preparation of polymer with SuFEx click reaction and RAFT

图式18. SuFEx点击反应与CuAAC聚合反应协同使用制备聚合物

Scheme 18. Preparation of polymer with SuFEx click reaction and CuAAC

图式19. SuFEx点击反应、CuAAC反应与Ugi缩合反应协同使用制备聚合物

Scheme 19. Preparation of polymer with SuFEx click reaction, CuAAC, and Ugi reaction

图式20. SuFEx点击反应对聚合物链端进行功能化改性

Scheme 20. Terminal modifications with SuFEx click reaction

图式21. SuFEx点击反应对聚合物侧链进行功能化改性

Scheme 21. Side-chain modifications with SuFEx click reaction

参考文献 29

[1]	Kolb H. C.; Finn M. G.; Sharpless K. B. Angew. Chem., Int. Ed. 2001, 40, 2004. doi: 10.1002/(ISSN)1521-3773
[2]	https://www.nobelprize.org/prizes/chemistry/2022/summary/
[3]	Dong J.; Krasnova L.; Finn M. G.; Sharpless K. B. Angew. Chem., Int. Ed. 2014, 53, 9430. doi: 10.1002/anie.v53.36
[4]	Dondoni A.; Marra A. Org. Biomol. Chem. 2017, 15, 1549. doi: 10.1039/C6OB02458K
[5]	Fattah T. A.; Saeed A.; Albericio F. J. Fluorine Chem. 2018, 213, 87. doi: 10.1016/j.jfluchem.2018.07.008
[6]	Barrow A. S.; Smedley C. J.; Zheng. Q.; Li S.; Dong J.; Moses J. E. Chem. Soc. Rev. 2019, 48, 4731. doi: 10.1039/c8cs00960k pmid: 31364998
[7]	Lekkala R.; Lekkala R.; Moku B.; Rakesh K. P.; Qin H.-L. Org. Chem. Front. 2019, 6, 3490. doi: 10.1039/C9QO00747D
[8]	Xu L.; Dong J. Chin. J. Chem. 2020, 38, 414. doi: 10.1002/cjoc.v38.4
[9]	Lee C.; Cook A. J.; Elisabeth J. E.; Friede. N. C.; Sammis G. M.; Ball N. D. ACS Catal. 2021, 11, 6578. doi: 10.1021/acscatal.1c01201
[10]	Zheng J.; Mao Y.; Feng S.; Tian R. Chin. J. Chem. 2021, 39, 1843. doi: 10.1002/cjoc.v39.7
[11]	Ykman P.; Hall Jr. H. K. J. Organomet. Chem. 1976, 116, 153. doi: 10.1016/S0022-328X(00)91790-X
[12]	Gembus V.; Marsais F.; Levacher V. Synlett 2008, 1463.
[13]	Qin H.-L.; Zheng Q.; Bare G. A. L.; Wu P.; Sharpless K. B. Angew. Chem., Int. Ed. 2016, 55, 14155. doi: 10.1002/anie.v55.45
[14]	Smedley C. J.; Giel M.-C.; Molino A.; Barrow A. S.; Wilison D. J.; Moses J. E. Chem. Commun. 2018, 54, 6020. doi: 10.1039/C8CC03400A
[15]	Thomas J.; Fokin V. V. Org. Lett. 2018, 20, 3749. doi: 10.1021/acs.orglett.8b01309 pmid: 29906123
[16]	Ungureanu A.; Levens A.; Candish L.; Lupton D. A. Angew. Chem., Int. Ed. 2015, 54, 11780. doi: 10.1002/anie.v54.40
[17]	Liu C.; Yang C.; Hwang S.; Ferraro S. L.; Flynn J. P.; Niu J. Angew. Chem., Int. Ed. 2020, 59, 18435. doi: 10.1002/anie.v59.42
[18]	Li S.; Wu P.; Moses J. E.; Sharpless K. B. Angew. Chem., Int. Ed. 2017, 56, 2903. doi: 10.1002/anie.v56.11
[19]	Gao B.; Li S.; Wu P.; Moses J. E.; Sharpless K. B. Angew. Chem., Int. Ed. 2018, 57, 1939. doi: 10.1002/anie.v57.7
[20]	Liang D.-D.; Streefkerk D. E.; Jordaan D.; Wagemakers J.; Baggerman J.; Zuilhof H. Angew. Chem., Int. Ed. 2020, 59, 7494. doi: 10.1002/anie.v59.19
[21]	Dong J.; Sharpless K. B.; Kwisnek L.; Oakdale J. S.; Fokin V. V. Angew. Chem., Int. Ed. 2014, 53, 9466. doi: 10.1002/anie.v53.36
[22]	Gao B.; Zhang L.; Zheng Q.; Zhou F.; Klivansky L. M.; Lu J.; Liu Y.; Dong J.; Wu P.; Sharpless K. B. Nat. Chem. 2017, 9, 1083. doi: 10.1038/nchem.2796
[23]	Wang H.; Zhou F.; Ren G.; Zheng Q.; Chen H.; Gao B.; Klivansky L.; Liu Y.; Wu B.; Xu Q.; Lu J.; Sharpless K. B.; Wu P. Angew. Chem., Int. Ed. 2017, 56, 11203. doi: 10.1002/anie.v56.37
[24]	Li S.; Li G.; Gao B.; Pujari S. P.; Chen X.; Kim H.; Zhou F.; Klivansky L. M.; Liu Y.; Driss H.; Liang D.-D.; Lu J.; Wu P.; Zuilhof H.; Moses J.; Sharpless K. B. Nat. Chem. 2021, 13, 858. doi: 10.1038/s41557-021-00726-x
[25]	Brendel J. C.; Martin L.; Zhang J.; Perrier S. Polym. Chem. 2017, 8, 7475. doi: 10.1039/C7PY01636K
[26]	Yang C.; Flynn J. P.; Niu J. Angew. Chem., Int. Ed. 2018, 57, 16194. doi: 10.1002/anie.v57.49
[27]	Li Z.; Ren X.; Sun P.; Ding H.; Li S.; Zhao Y.; Zhang K. ACS Macro Lett. 2021, 10, 223. doi: 10.1021/acsmacrolett.0c00812
[28]	Li S.; Beringer L. T.; Chen S.; Averick S. Polymer 2015, 78, 37. doi: 10.1016/j.polymer.2015.09.055
[29]	Oakdale J. S.; Kwisnek L.; Fokin V. V. Macromolecules 2016, 49, 4473. doi: 10.1021/acs.macromol.6b00101