Recent Advances in N-Arylation of NH-Sulfoximines and Their Applications

doi:10.6023/cjoc202110011

Abstract

Sulfoximines represent an important structural motif in organic chemistry, and have been utilized as chiral auxiliaries, chiral ligands and organocatalysts. They also serve as key intermediates for the construction of heterocyclic compounds. Attributing to their unique bioactivities, sulfoximines have been developed as previliged pharmacophores and widely used in pharmaceutical chemistry and agriculture. Considering the wide applications, the synthetic methods to afford sulfoximines have attracted increasing attention. Among them, the direct arylation of NH-sulfoximines to prepare NAr- sulfoxmines exhibites some unique advantages, including atom-economics, mild conditions and step-economics, and thus has made tremedous progress in recent years. Various methods of NH-sulfoximines to afford NAr-sulfoximines via a C—N bond formation strategy, as well as their applications in synthesis of bioactive molecules and ligands for transition-metal catalysts, are reviewed.

Key words: NH-sulfoximine, N-arylation, NAr-sulfoximine, C—N bond formation

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Xue Li, Cong Wang, Tiezheng Jia. Recent Advances in N-Arylation of NH-Sulfoximines and Their Applications[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 714-731.

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Fig. & Tab. 22

Scheme 1. Representative examples of bioactive sulfoximines

Scheme 3. One-pot-two-steps synthesis of N-arylated sulfoximines

Scheme 4. Copper-catalyzed direct arylation of NH-sulfoximines with azoles and polyfluoroarenes

Scheme 6. Proposed mechanism for Chan-Lam coupling of NH- sulfoximine and arylboronic acid

Scheme 11. One-pot one-operation synthesis of benzothiazine

Scheme 12. Palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenylallyl acetates with dimethyl malonate

Scheme 13. Synthetic route of bis(sulfoximine) ligand

Scheme 14. Copper-catalyzed hetero-Diels-Alder reactions

Scheme 15. Copper-catalyzed asymmetric Mukaiyama-aldol reactions

Scheme 16. Synthetic route of aminosulfoximine ligands

Scheme 17. Ir-catalyzed asymmetric imine hydrogenation

Scheme 18. Synthesis of [Ir(cod)(100-102a-c)]BArF catalyst precursors

Scheme 19. Asymmetric hydrogenation of olefins tethering poorly coordinative groups

Scheme 20. Synthesis of stereogenic center at benzylic position via a sulfoximine addition strategy

Scheme 21. Synthetic route of 3,4-dihydroquinolin-2(1H)-one (117)

Scheme 22. Substrate scope for stereoselective synthesis of 4-aminobenzothiazines Reaction conditions: (a) 5 mol% Pd2(dba)3, 7.5 mol% Xanthphos, 2.0 equiv. Cs2CO3, 1,4-dioxane, 100 oC, 2 h; (b) 2.0 equiv. LiHMDS (1 mol/L in THF), –78 oC, 2 h; (c) HCl (4 mol/L in 1,4-dioxane), MeOH, 0 oC, 2 h.

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