Application of Photosensitizer 2, 4, 5, 6-Tetrakis(carbazol-9-yl)-1, 3-dicyanobenzene in Photo-induced Transition-Metal-Free Organic Synthesis

doi:10.6023/cjoc201904022

Abstract

Visible-light-promoted organic synthesis is an important research hotspot and frontier in organic chemistry in recent years. Particularly, as a novel organic photosensitizer, 2, 4, 5, 6-tetrakis(carbazol-9-yl)-1, 3-dicyanobenzene (4CzIPN) has showed excellent catalytic performance in visible-light-induced radical reactions. The recent progress on the transition-metal-free photosynthesis under visible-light catalyzed by 4CzIPN is reviewed, and the application of 4CzIPN for photocatalytic organic transformations from different precursors (including silicon reagent, carboxylic acid and its derivatives, sulfur-containing reagent and fluorine reagent) is included.

Key words: 2, 4, 5, 6-tetrakis(carbazol-9-yl)-1, 3-dicyanobenzene (4CzIPN), organophotocatalyst, visible-light-induced, metal-free

Cite this article

Chen Jinyang, Li Yuhan, Mei Lan, Wu Hongyu. Application of Photosensitizer 2, 4, 5, 6-Tetrakis(carbazol-9-yl)-1, 3-dicyanobenzene in Photo-induced Transition-Metal-Free Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3040-3050.

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Fig. & Tab. 24

Figure 1. Structure of 2, 4, 5, 6-tetrakis(carbazol-9-yl)-1, 3- dicyanobenzene (4CzIPN)

^a Conditions: All the potentials are relative to SCE (saturated calomel electrode), CH₃CN, room temperature.

Compd.	E_1/2(P⁺/ P*)/V	E_1/2(P*/ P^-)/V	E_1/2(P⁺/ P)/V	E_1/2(P/ P^-)/V
4CzIPN	-1.04	+1.35	+1.52	-1.21
曙红Y	-1.11	+0.83	+0.78	-1.06
孟加拉玫瑰红	-0.99	+0.66	+0.78	-1.11
亚甲基蓝		+1.48		+0.11
10-甲基-9-均三甲苯基吖啶盐		+2.06		-0.57
啶盐

Table 1. Redox potentials of common organophotocatalysts

Schema 1. 4CzIPN-catalyzed defluorinative alkylation reaction

Schema 2. 4CzIPN-catalyzed cyclopropanation reaction

Schema 3. 4CzIPN-catalyzed catalyzed cyclopropanation reaction

Schema 4. 4CzIPN-catalyzed Si-H functionalization

Schema 5. 4CzIPN-catalyzed hydrosilylation of olefins

Schema 6. 4CzIPN-catalyzed difunctionalization of olefins

Schema 7. 4CzIPN-catalyzed alkylation of imines

Schema 8. 4CzIPN-catalyzed carbonylation of alkyl radicals

Schema 9. 4CzIPN-catalyzed hydroformylation of olefins

Schema 10. 4CzIPN-catalyzed one-pot stepwise Minisci reaction

Schema 11. 4CzIPN-catalyzed oxidative decarboxylation coupling

Schema 12. 4CzIPN-catalyzed difunctionalization of unactivated alkene

Schema 13. 4CzIPN-catalyzed decarboxylation coupling reaction

Schema 14. 4CzIPN-catalyzed trifluoromethylthiolation of tertiary ethers

Schema 15. 4CzIPN-catalyzed radical cascade reactions

Schema 16. 4CzIPN-catalyzed synthesis of α, α-difluoroketone hydrazones

Schema 17. 4CzIPN-catalyzed selenation cyclization

Schema 18. 4CzIPN-catalyzed synthesis of 1, 5-dicarbonyl compounds

Schema 19. 4CzIPN-catalyzed synthesis of chlorinated arenes

Schema 20. 4CzIPN-catalyzed synthesis of cycloalkanes

Schema 21. 4CzIPN-catalyzed remote C—H functionalization

Schema 22. 4CzIPN-catalyzed hydrocarboxylation of imines

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