Recent Advances in the Functionalization of para-C(sp2)—H Bonds of Anilines

doi:10.6023/cjoc202511017

Abstract

The direct functionalization of the para-C(sp²)—H bond of anilines represents a significant research direction in organic synthesis. Conventionally, achieving selective functionalization at this position has predominantly relied on the pre-protection and activation of the amino group, a process that is not only step-intensive but also severely limits synthetic efficiency and step economy. In recent years, revolutionary progress has been made in this field. The development of diverse strategies, such as transition metal catalysis, organic photoredox catalysis, electrochemical synthesis, and metal-free catalysis, has successfully enabled the direct and highly selective modification of the para-C—H bond of anilines, fundamentally overcoming the limitations of traditional approaches. This review aims to systematically outline the research trajectory in this area, providing a detailed summary of the reaction design, mechanistic characteristics, and applications of these catalytic modalities in constructing carbon-carbon and carbon-heteroatom bonds, thereby offering a comprehensive account of the current development and key achievements in this pivotal synthetic transformation.

Key words: anilines, C—H functionalization, site-selectivity, transition metal catalysis, photoredox catalysis

Cite this article

Lewei Dai, Jianling Wang, Dong Zou. Recent Advances in the Functionalization of para-C(sp²)—H Bonds of Anilines[J]. Chinese Journal of Organic Chemistry, 2026, 46(5): 1813-1844.

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Fig. & Tab. 45

Figure 1. Some drugs containing aromatic amine structures

Scheme 1. Copper-catalyzed para-selective C—H gem-difluoro olefination of aromatic amines

Scheme 2. Ag-catalyzed regioselective C—H bond alkylation of N,N-dialkylaniline with alkyneamine

Scheme 3. Palladium-catalyzed para-C—H arylation of anilines

Scheme 4. Palladium/Copper co-catalyzed synthesis of fused chromenoquinolines

Scheme 5. Gold-catalyzed carbon-carbon coupling reaction of carbazoles and methyl aryldiazoacetates

Scheme 6. CuCl2-catalyzed para-C—H alkylation of aniline derivatives

Scheme 7. Rh-catalyzed asymmetric coupling reaction of arylvinyldiazoacetates and arylamines

Scheme 8. Rhodium-catalyzed synthesis of chromene derivatives

Scheme 9. Palladium and rhodium co-catalyzed for the synthesis of all-carbon quaternary center compounds

Scheme 10. Rh(II)/Xantphos-catalyzed for the synthesis of all-carbon quaternary center compounds

Scheme 11. Base-promoted cobalt-catalyzed regio- and enantioselective para-Friedel-Crafts alkylation of aniline derivatives

Scheme 12. Copper-catalyzed cross coupling reaction of tertiary alkyl halides with anilines

Scheme 13. Ruthenium-catalyzed alkylarylation transformation of anilines, alkenes, and α-bromoalkanes

Scheme 14. Silver-catalyzed regioselective 1,6-hydroarylation of para-quinone methides with anilines

Scheme 15. Magnesium-catalyzed para-selective allylation of anilines with arylenes

Scheme 16. Iridium-catalyzed selective para-C-alkylation of anilines with aryl alkynes

Scheme 17. Iridium-catalyzed para-boroylation of anilines

Scheme 18. Iron-catalyzed direct para-halogenation reaction of anilines

Scheme 19. Electrocatalytic strategy for selective dehydrogenative cross-coupling of anilines and naphthalen-2-amine derivatives

Scheme 20. Electrochemical synthesis of symmetrical benzidines through dehydrogenative cross-coupling reaction

Scheme 21. An electrocatalytic three-component reaction for the synthesis of phosphoroselenoates

Scheme 22. Iodine-mediated thioarylation under electrochemical conditions

Scheme 23. Visible-light-mediated ruthenium-catalyzed para-selective alkylation of unprotected anilines

Scheme 24. Organic photocatalysis para-selective coupling of aniline derivatives with azo compounds

Scheme 25. HFIP-catalyzed hydroarylation of olefins

Scheme 26. Acid-catalyzed (a) trifluoromethylarylation (b) arylation of alkenes using anilines

Scheme 27. Boron-catalyzed hydroarylation of 1,3-dienes with arylamines

Scheme 28. B(C6F5)3 and HFIP synergistically catalyzed bisarylation reaction

Scheme 29. Synthesis of structurally diverse HFIP functionalized aniline derivatives

Scheme 30. HFIP-promoted high selectivity hydroxyalkylation reaction of aniline derivatives with arylglyoxylate hydrates

Scheme 31. HFIP-mediated synthesis of triarylmethane derivatives

Scheme 32. Synthesis of triarylmethane derivatives via HFIP- mediated 1,6-hydroarylation reaction

Scheme 33. Borane-catalyzed divergent para and ortho C-alky- lation of arylamines using benzylic alcohols

Scheme 34. CPA-catalyzed enantioselective para-addition of anilines to ketimines

Scheme 35. CPA-catalyzed enantioselective para-addition of anilines to cyclic thioimidates

Scheme 36. CPA-catalyzed asymmetric synthesis of triphenylmethanes

Scheme 37. Chiral phosphoric acid-mediated para-selective functionalization of diphenylamines with propargylic 3-methyleneindoles

Scheme 38. Imidazonium catalyzed coupling reaction of allyl alcohols with anilines

Scheme 39. Brønsted acidic ionic liquid catalyzed Friedel-Crafts reaction

Scheme 40. Iodine-catalyzed para-sulfurization reaction of ani- lines

Scheme 41. Iodine/DMSO-promoted selective direct arylthiation of anilines

Scheme 42. Iodine-mediated site-selective C—H chalcogenation of carbazoles

Scheme 43. H2O/DMSO-promoted para-C—H heteroarylation of anilines

Scheme 44. para-Bromination reaction of anilines

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芳胺对位C(sp²)—H键官能团化研究进展

Recent Advances in the Functionalization of para-C(sp²)—H Bonds of Anilines

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芳胺对位C(sp2)—H键官能团化研究进展