Application of Triaryl Carbenium in Organic Synthesis

doi:10.6023/cjoc202308007

Abstract

Triaryl carbenium, known as an exceptional Lewis acid, possesses a low-lying lowest unoccupied molecular orbital (LUMO) that readily accepts an electron pair, which was widely used in synthetic transformations serving as reagent or catalyst. Over the past decade, triaryl carbenium has been used as catalyst, pre-catalyst, co-catalyst and additive in organic synthesis. Moreover, triaryl carbenium as a key intermediate approached to the successful synthesis of tetra-arylmethane. In this review, the application progress of triaryl carbenium in organic synthesis in recent years is summarized, and its diverse functional roles in organic synthesis are summarized, hoping to attract widespread attention.

Key words: triaryl carbenium, catalysis, organic synthesis, metal-free

Cite this article

Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.

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Fig. & Tab. 31

Scheme 1. [Tr]＋[BF4]—-catalyzed Diels-Alder and Michael addition reactions[10]

Scheme 2. Franzén’s [Tr]＋[BF4]—-catalyzed organic transformations[11]

Scheme 3. [Tr]＋[BF4]—-catalyzed oxa-Diels-Alder and oxo-Metathesis reactions[12-13]

Scheme 4. [Tr]＋[BF4]— catalyzed bromination of arenes[14]

Scheme 5. [Tr]＋[BF4]—?catalyzed 1,2-hydride migration and 1,6-addition reactions[15-16]

Scheme 6. [Tr]＋[BF4]—?catalyzed cycloaddition and ring-opening reactions[17??-20]

Scheme 7. Triaryl carbenium ion-pair catalyzed intramolecular carbonyl-ene cyclization and [2＋2] cycloaddition reactions[21]

Scheme 8. [Tr]＋[B(C6F5)4]— catalyzed Diels-Alder reaction with anthracene derivatives[22]

Scheme 9. [Tr]＋[B(C6F5)4]— catalyzed intermolecular formal [2＋2＋1] cycloaddition reaction[23]

Scheme 10. [Tr]＋[B(C6F5)4]— catalyzed hydroarylation of alkenes and Hosomi-Sakurai reaction[24-25]

Scheme 11. In-situ synthesis of triaryl carbenium from chiral triphosphate catalyzed asymmetric reactions[27]

Scheme 12. Application of triaryl carbenium in the asymmetric Diels-Alder reaction of anthracene[28]

Scheme 13. Intramolecular hydroarylation of β?benzylstyrenes[29]

Scheme 14. Intermolecular C—H insertion reaction[30]

Scheme 15. Intramolecular C—H insertion reaction[31]

Scheme 16. Friedel-Crafts and Pictet-Spengler reactions used [Tr]＋[B(C6F5)4]— as pre-catalyst in water[32-33]

Scheme 17. Synthesis of β-carbolines used [Tr]＋[B(C6F5)4]— as pre-catalyst[34]

Scheme 18. [Tr]＋[B(C6F5)4]—-combined with yttrium catalyzed ortho-selective C—H alkylation of N,N-dimethyl anilines[36]

Scheme 19. [Tr]＋[B(C6F5)4]—-combined with yttrium catalyzed C(sp3)—H activation of 2-methyl azaarenes[37]

Scheme 20. [Tr]＋[B(C6F5)4]— initiated intramolecular hydrosilylation of alkynylphenylsilanes[38]

Scheme 21. [Tr]＋[B(C6F5)4]— initiated hydrostannylation[39]

Scheme 22. [Tr]＋[B(C6F5)4]— initiated Friedel-Crafts alkylation and annulation reaction[40-41]

Scheme 23. [Tr]＋[B(C6F5)4]— initiated intramolecular Friedel- Crafts-type cyclization of 1,1-difluoroalkenes[42]

Scheme 24. Synthesis of phosphine compounds initiated by [Tr]＋[B(C6F5)4]—[43]

Scheme 25. Metal-free cyanosilylation of ketones used Ph3C＋[B(C6F5)4]— as pre-catalyst[44]

Scheme 26. Synthesis of triarylmethane using triaryl carbenium ion-pair as co-catalyst[45]

Scheme 27. [Tr]＋[BF4]—-mediated single C—F bond cleavage reaction[46]

Scheme 28. [Tr]＋[BF4]—-mediated single C—F bond cleavage reaction for the synthesis of difluoromethylenes[47]

Scheme 29. Asymmetric synthesis of tetraarylmethanes via triaryl carbenium intermediates[48]

Scheme 30. Asymmetric substitution reaction of triaryl methanol with indoles via triaryl carbenium intermediates[49]

Scheme 31. Asymmetric substitution reaction of triaryl methanol[50]

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