Advances of N-Hydroxyphthalimide Esters in Photocatalytic Alkylation Reactions

doi:10.6023/cjoc202105041

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4661-4689.DOI: 10.6023/cjoc202105041 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑；绿色合成化学专辑；热点论文虚拟合集

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贺帅旗^a, 李昊聪^a, 陈晓岚^a^,^*(), Igor B. Krylov^b, Alexander O. Terent'ev^b^,^*(), 屈凌波^a, 於兵^a^,^*()

a 郑州大学化学学院绿色催化中心郑州 450001
b 俄罗斯科学院泽林斯基有机化学研究所莫斯科 119991 俄罗斯

收稿日期:2021-05-23 修回日期:2021-06-07 发布日期:2021-06-08
通讯作者: 陈晓岚, Alexander O. Terent'ev, 於兵
作者简介:
† 共同第一作者
基金资助:
国家自然科学基金(21971224); 国家自然科学基金(22071222); 高等学校学科创新引智计划(111项目); 高等学校学科创新引智计划(D20003); 河南省高校重点科研(20A150006); 河南省高校重点科研(21A150053); 河南省自然科学基金(202300410375)

Advances of N-Hydroxyphthalimide Esters in Photocatalytic Alkylation Reactions

Shuaiqi He^a, Haocong Li^a, Xiaolan Chen^a(), Igor B. Krylov^b, Alexander O. Terent'ev^b(), Lingbo Qu^a, Bing Yu^a()

a Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, China
b Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 119991, Russian Federation

Received:2021-05-23 Revised:2021-06-07 Published:2021-06-08
Contact: Xiaolan Chen, Alexander O. Terent'ev, Bing Yu
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21971224); National Natural Science Foundation of China(22071222); Programme of Introducing Talents of Discipline to Universities(111项目); Programme of Introducing Talents of Discipline to Universities(D20003); Key Research Projects of Universities in Henan Province(20A150006); Key Research Projects of Universities in Henan Province(21A150053); Natural Science Foundation of Henan Province(202300410375)

N-Hydroxyphthalimide (NHP) esters are easily available, stable, inexpensive, and highly photoactive compounds, which are derived from the corresponding carboxylic acids. In recent years, the application of NHP esters in photocatalytic decarboxylative reactions has captured huge attention. Herein, the vigorous development of photocatalytic alkylation reactions using alkyl NHP esters as alkylating reagents is summarized based on the classification of photocatalysts.

Key words: N-hydroxyphthalimide (NHP) ester, photocatalytic, decarboxylation, alkylation, photocatalyst

Cite this article

Shuaiqi He, Haocong Li, Xiaolan Chen, Igor B. Krylov, Alexander O. Terent'ev, Lingbo Qu, Bing Yu. Advances of N-Hydroxyphthalimide Esters in Photocatalytic Alkylation Reactions[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4661-4689.

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Fig. & Tab. 49

Scheme 1. Activation modes and application of NHP esters in the photocatalytic alkylation reaction

Scheme 2. Photocatalytic Michael addition of NHP esters with electron-deficient olefins

Scheme 3. Photocatalytic decarboxylation involved in NHP esters in the synthesis of natural product (–)-aplyviolene

Scheme 4. Photocatalytic decarboxylative coupling of alkyl N-phthalimidoyl oxalates with Ru-photocatalyst

Scheme 5. Synthesis of alkyl-substituted alkynes via photocatalytic alkylation of NHP esters with alkynyl sulfones

Scheme 6. Visible-light-induced decarboxylative alkylation/ cyclization of tertial alkyl NHP esters with N-arylacrylamides

Scheme 7. Synthesis of phenanthridine derivatives via decarboxylative alkylation/cyclization of NHP esters with 2-isocyanobiphenyl compounds

Scheme 8. Three-component alkylamination of olefins via Ru-photoredox catalysis

Scheme 9. Photocatalytic Minisci-type C—C coupling of NHP esters with N-heterocyclic compounds in the presence of Ru- photocatalyst

Scheme 10. Synthesis of alkyl functionalized non-aromatic heterocycles through NHP esters as alkylation reagents

Scheme 11. Photocatalytic formation of C—X (X=heteroatoms) bonds based on NHP esters in the presence of metal photocatalysts

Scheme 12. Photocatalytic decarboxylative alkylation of NHP esters with N-heteroarenes in the presence of Ir-photocatalyst

Scheme 13. Photocatalytic dual decarboxylative coupling of NHP esters with α,β-unsaturated carboxylic acids

Scheme 14. Synthesis of organoboron compounds via photocatalytic decarboxylation of NHP esters in the presence of Ir-photocatalyst

Scheme 15. Photocatalytic alkylation/lactonization of NHP esters with unsaturated carboxylic acids

Scheme 16. Synthesis of ketones via photocatalytic alkylation of NHP esters with olefins

Scheme 17. Synthesis of cyclic ketones through photocatalytic cascade cyclization of NHP esters

Scheme 18. Photocatalytic asymmetric cyanation reaction involving NHP esters catalyzed by Ir/Cu dual catalytic system.

Scheme 19. Photocatalytic Minisci-type asymmetric coupling of NHP esters with N-heterocyclic compounds in the presence of Ir-photocatalyst

Scheme 20. Photocatalytic C—O cross-coupling of NHP esters with phenols in Ir/Cu dual catalytic system

Scheme 21. Stereoselective synthesis of alkylated olefins via Ir-photocatalyst

Scheme 22. Photocatalytic alkylation of coumarin C-3 site involving NHP esters

Scheme 23. Synthesis of polycyclic heterocycles through 1,5-hydrogen atom transfer process involving NHP esters

Scheme 24. Three-component alkylamination of styrenes via Ir-photoredox catalysis

Scheme 25. Synthesis of aldehydes via photocatalytic decarboxylation of specific NHP ester and N-heterocycles

Scheme 26. Light-induced nucleophilic fluorination of NHP esters

Scheme 27. Photocatalytic site-selective difluoroalkylation of NHP esters in the presence of Ir-photocatalyst

Scheme 28. Cu-catalyzed synthesis of protected amines via decarboxylative C—N coupling of NHP esters

Scheme 29. Cu-catalyzed intermolecular decarboxylative C(sp3)—C(sp3) cross-coupling of NHP esters with glycine and peptides

Scheme 30. Cu-catalyzed decarboxylative coupling of NHP esters with heteroarenes

Scheme 31. Cu-catalyzed synthesis of alkyl-substituted alkynes via photocatalytic alkylation of NHP esters with terminal alkynes

Scheme 32. Photocatalytic decarboxylative coupling of NHP esters with olefins or alkynes in the presence of Eosin Y

Scheme 33. Photocatalytic radical cascade cyclization of NHP esters in the presence of Eosin Y

Scheme 34. Eosin Y-catalyzed photocatalytic alkylation of specific sites of classic heteroarenes involving NHP esters

Scheme 35. Photocatalytic decarboxylative coupling of NHP esters in the presence of 4CzIPN

Scheme 36. Photocatalytic selective alkylation/cyclization of NHP esters with alkynylphosphine oxides in the presence of Eosin B

Scheme 37. Synthesis of N-alkyl hydrazones via decarboxylative C(sp3)—N coupling of NHP esters with α-diazoacetates in the presence of Rose Bengal

Scheme 38. Organophotoredox-catalyzed decarboxylation of NHP esters for the construction of C(sp3)—O—C(sp3) fragment in the presence of N-Ar-phenothiazine

Scheme 39. Photocatalytic decarboxylative thiolation of NHP esters for the synthesis of free thiols in the presence of Eosin Y-Na2

Scheme 40. Semiconductor mediated heterogeneous photocatalytic decarboxylation of NHP esters

Scheme 41. Synthesis of aryl sulfides via decarboxylative coupling without photocatalysts

Scheme 42. Visible-light-induced decarboxylative intramolecular or intermolecular coupling of NHP esters using thiophenol as an organic catalyst

Scheme 43. Synthesis of boronic esters via decarboxylative C—B coupling of NHP esters with diboronate esters

Scheme 44. Pd-catalyzed radical approach for the synthesis of π-allylpalladium complexes involving NHP esters

Scheme 45. Application of EDA system composed of NHP esters and HE in the photocatalytic decarboxylation of NHP esters

Scheme 46. 3-Acetoxyquinuclidine mediated photocatalytic single electron transfer of NHP esters

Scheme 47. Decarboxylative coupling of NHP esters with silyl enol ethers or N-heterocycles mediated by PPh3/NaI system

Scheme 48. Decarboxylative coupling of NHP esters with 1,1-diarylethylene or cinnamic acid derivatives using PPh3/NaI catalysis

Scheme 49. Decarboxylative cyclization reaction of NHP esters with 1,7-enynes mediated by PCy3/KI system

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N-羟基邻苯二甲酰亚胺酯在光催化烷基化反应中的研究进展

Advances of N-Hydroxyphthalimide Esters in Photocatalytic Alkylation Reactions

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