Recent Development of SuFEx Reaction between Silyl Ethers and Sulfur(VI) Fluoride Compounds

doi:10.6023/cjoc202304026

Abstract

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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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Fig. & Tab. 21

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 13. DBU-catalyzed synthesis of polysulfates and polysulfonates

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

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

Scheme 16. DBU-catalyzed synthesis of polysulfluoridoimidiate

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

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

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

Scheme 20. Terminal modifications with SuFEx click reaction

Scheme 21. Side-chain modifications with SuFEx click reaction

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硅醚与硫(VI)氟化合物SuFEx点击反应进展