N-碘代丁二酰亚胺(NIS)参与的碘化反应最新研究进展

doi:10.6023/cjoc202306026

摘要/Abstract

有机碘化合物是一类非常重要的功能性分子, 其合成研究具有重要意义. 鉴于N-碘代丁二酰亚胺(NIS)具有反应活性高、廉价易得和环境友好等优点, 一直以来都是碘化反应的优选碘试剂. 近年来利用NIS参与的碘化反应制备有机碘化合物有了重要新进展, 引起了极大地关注. 综述了这一领域的最新研究进展, 主要包括NIS与芳烃/末端炔烃的C—H碘化反应、NIS与不饱和化合物和亲核试剂的碘化双官能团化反应, 以及NIS与不饱和化合物的串联碘环化反应.

关键词: 碘化反应, N-碘代丁二酰亚胺(NIS), 有机碘化合物

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

引用此文

曹同阳, 李玮, 王力竞. N-碘代丁二酰亚胺(NIS)参与的碘化反应最新研究进展[J]. 有机化学, 2024, 44(2): 508-524.

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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图/表 42

图式1. BF3-H2O促进的非活性芳烃的碘化反应

Scheme 1. BF3-H2O promoted iodization of deactivated arenes

图式 2. In催化下天然产物芳烃的C—H碘化反应

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

图式3. 过渡金属催化的芳烃C—H碘化反应

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

图式4. Pd(OAc)2催化下芳烃的选择性C—H碘化反应

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

图式5. 过渡金属催化的苯甲酰胺类化合物的邻位C—H碘化反应

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

图式6. 嘧啶诱导的芳烃选择性C—H碘化反应

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

图式7. 钯催化芳香偶氮化合物的区域选择性C—H碘化反应

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

图式8. 邻位碘化含苝二酰亚胺的合成

Scheme 8. Synthesis of ortho-iodinated perylene diimides

图式9. Ir催化苯甲酸的邻位C—H碘化反应

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

图式10. Rh(III)催化1-芳基异喹啉的不对称C—H碘化反应

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

图式11. 1-(2H)-二氮杂萘酮在C(8)位置的C—H碘化反应

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

图式12. 对甲苯磺酸(PTSA)催化的噻吩衍生物碘化反应

Scheme 12. PTSA-catalyzed iodization of thiophene derivatives

图式13. 吲哚的区域选择性C(5)—H碘化反应

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

图式14. PTSA催化异喹啉-1(2H)-酮的区域选择性C(4)—H碘化反应

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

图式15. 末端炔烃和NIS的C—H碘化反应

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

图式16. 炔与1H-苯并三唑和NIS的加成反应

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

图式 17. 烯烃与NH-1,2,3-三氮唑的N2-选择性碘代双官能化反应

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

图式18. 烯烃与唑类化合物以及NIS的碘代双官能化反应

Scheme 18. Iododifunctionalization of alkenes with azoles and NIS

图式 19. NIS与磺胺类化合物的分子间碘胺化反应

Scheme 19. Intermolecular iodization of NIS with sulfonamides

图式 20. NIS介导的NH-1,2,3-三氮唑与丙二烯酰胺的N2选择性烯丙基化反应

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

图式21. 炔类化合物的碘化磺酰化双官能团化反应

Scheme 21. Iodosulfonation reaction of alkynes

图式22. NIS促进下环丙基胺的碘化双官能团化反应

Scheme 22. NIS-promoted iododifunctionalization of cyclopropylamines

图式23. NIS诱导的烯烃与P(O)—OH键的区域选择性碘磷酰氧化反应

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

图式 24. 三组分傅克反应：烯基碘化物的合成

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

图式25. NIS介导下3-硅氧基烯炔的亲电碘环化反应

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

图式26. 有机催化剂促进烯丙醇的对映选择性3-exo碘环化醚化反应

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

图式27. Ph3P催化的碘环化反应:合成3-碘吲哚和3-碘苯并[b]呋喃

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

图式28. 炔醇/炔胺与NIS的亲电串联碘环化反应

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

图式 29. NIS参与的三组分反应合成三氟甲基化碘代异噁唑衍生物

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

图式30. NIS参与的三组分反应合成三氟甲基化碘代咪唑啉衍生物

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

图式31. 吲哚类化合物分子内螺环化碘环化反应

Scheme 31. Intramolecular spiral iodoyclization of indoles

图式32. [3＋2]环加成反应合成三取代碘代呋喃

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

图式33. NIS/HFIP介导下炔丙基硫化物的串联碘环化反应

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

图式35. NIS促进下苯甲酰亚胺高烯丙酯的选择性氨基-双叠氮化和氨基-碘叠氮化反应

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

图式36. NIS促进下苯甲酰亚胺高烯丙酯的区域选择性7-endo或6-exo碘环化反应

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

图式37. NIS和TMSN3介导下酰胺的自由基碘环化反应

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

图式38. 1,7-烯炔的自由基碘代叠氮化反应

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

图式39. 太阳光促进炔酸酯与NIS的碘环化反应

Scheme 39. Sunlight-promoted iodocyclization of alkynates with NIS

图式40. 烯基肟的氧碘化反应

Scheme 40. Oxyiodonalization of allylic oximes

图式41. 光驱动下1,5-烯炔与TMSN3和NIS的碘代叠氮化反应

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

图式42. 光催化下N-苄基丙炔酰胺与NIS的碘化螺环化反应

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

图式43. [3＋2]环加成反应:合成碘化吡咯烷

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

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