Recent Progress in N-Iodosuccinimide (NIS)-Mediated Iodination Reactions

doi:10.6023/cjoc202306026

Abstract

Organoiodine compounds belong to a very important class of functional molecules and their synthesis research is of great significance. Given the advantages of N-iodosuccinimide (NIS) with high reactivity, cheap and easy to get and environmental friendliness, it has always been the preferred iodine reagent for iodization, and in recent years, the preparation of organic iodine compounds by iodization reaction with NIS has made great progress, which has received considerable interest. To this end, the research progress is summarized, including the C—H iodization of NIS and aromatics/terminal alkynes, iodine difunctionalization between NIS and unsaturated compounds with nucleophiles, and cascade iodocyclization between NIS and unsaturated compounds.

Key words: iodization, N-iodosuccinimide, organoiodine compounds

Cite this article

Tongyang Cao, Wei Li, Lijing Wang. Recent Progress in N-Iodosuccinimide (NIS)-Mediated Iodination Reactions[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 508-524.

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Fig. & Tab. 42

Scheme 1. BF3-H2O promoted iodization of deactivated arenes

Scheme 2. In-catalyzed C—H iodization of natural aromatics

Scheme 3. Transition metal-catalyzed C—H iodization of aro- matics

Scheme 4. Pd(OAc)2-catalyzed selective C—H iodization of aromatics

Scheme 5. Transition metal-catalyzed ortho-C—H iodization of benzoamide compounds

Scheme 6. Pyrimidine-induced selective C—H iodization of aromatics

Scheme 7. Palladium-catalyzed regioselective C—H iodization of aromatic azo compounds

Scheme 8. Synthesis of ortho-iodinated perylene diimides

Scheme 9. Ir-catalyzed ortho-C—H iodination of benzoic acids

Scheme 10. Rh(III)-catalyzed asymmetric C—H iodination of 1-aryl isoquinolines

Scheme 11. C(8)—H iodination of 1-(2H)-phthalazinones

Scheme 12. PTSA-catalyzed iodization of thiophene derivatives

Scheme 13. Regioselective C(5)—H iodination of indoles

Scheme 14. PTSA-catalyzed the regioselective C(4)—H iodization of isoquinolin-1(2H)-ketones

Scheme 15. C—H iodization of terminal alkynes with NIS

Scheme 16. Acetylene addition reaction with 1H-benzotriazole and NIS

Scheme 17. N2-Selective iododifunctionalization of alkenes with NH-1,2,3-triazoles

Scheme 18. Iododifunctionalization of alkenes with azoles and NIS

Scheme 19. Intermolecular iodization of NIS with sulfonamides

Scheme 20. NIS-mediated N2-selective allylation of NH-1,2,3- triazoles with allenamides

Scheme 21. Iodosulfonation reaction of alkynes

Scheme 22. NIS-promoted iododifunctionalization of cyclopropylamines

Scheme 23. NIS-induced regioselective iodophosphoryloxylation of alkenes with P(O)—OH bonds

Scheme 24. Three-component Friedel-Crafts reaction: synthesis of alkenyl iodides

Scheme 25. NIS-mediated electrophilic iodocyclization of 3-siloxy-enyne

Scheme 26. Organocatalyst-promoted enantioselective 3-exoiodo-cycloetherification of allyl alcohols

Scheme 27. Ph3P-catalyzed iodocyclization for the synthesis of 3-iodoindole and 3-iodobenzo[b]furan

Scheme 28. Electrophilic tandem iodocyclization of acetynols/acetynoamines with NIS

Scheme 29. NIS-promoted three-component reaction for the synthesis of trifluoromethyl iodoisooxazoles

Scheme 30. NIS-promoted three-component reaction for the synthesis of trifluoromethyl iodoimidazoline

Scheme 31. Intramolecular spiral iodoyclization of indoles

Scheme 32. Synthesis of trisubstituted iodofuran via [3＋2] cycloaddition

Scheme 33. NIS/HFIP-mediated tandem iodocyclization of propargylic sulfides

Scheme 35. NIS-promoted selective amino-diazidation and amino-iodoazidation of O?homoallyl benzimidates

Scheme 36. NIS-promoted regioselective 7-endo or 6-exo iodocyclization of O-homoallyl benzimidates

Scheme 37. NIS and TMSN3-mediated radical iodocyclization of amides

Scheme 38. Radical iodoazide reactions of 1,7-enynes

Scheme 39. Sunlight-promoted iodocyclization of alkynates with NIS

Scheme 40. Oxyiodonalization of allylic oximes

Scheme 41. Light-promoted iodoazidation of 1,5-enynes with TMSN3 and NIS

Scheme 42. Photocatalytic iodospirocyclization of N-benzyl proparynamide with NIS

Scheme 43. [3＋2] annulations for the synthesis of iodopyrrolidines

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N-碘代丁二酰亚胺(NIS)参与的碘化反应最新研究进展