芳胺对位C(sp2)—H键官能团化研究进展

doi:10.6023/cjoc202511017

摘要/Abstract

芳胺对位C(sp²)—H键的直接官能团化是有机合成领域中的一个重要研究方向. 传统上, 实现该位点的选择性官能团化主要依赖于氨基的预保护与活化, 此过程不仅步骤繁琐, 且严重制约了合成的效率与步骤经济性. 近年来, 该领域取得了革命性进展, 通过发展过渡金属催化、有机光催化、电化学合成以及无金属催化等多元化策略, 成功实现了芳胺对位C—H键的直接、高选择性修饰, 从根本上克服了传统方法的局限性. 此文旨在系统梳理这一领域的研究脉络, 详细总结了上述各类催化模式的反应设计、机理特点及其在构建C—C与C—杂原子键中的应用, 并对该关键合成转化的发展现状与核心成就进行了全面评述.

关键词: 苯胺, C—H官能团化, 位点选择性, 过渡金属催化, 光催化

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

引用此文

戴乐薇, 王建玲, 邹东. 芳胺对位C(sp²)—H键官能团化研究进展[J]. 有机化学, 2026, 46(5): 1813-1844.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 45

图1. 一些含有芳胺结构的药物

Figure 1. Some drugs containing aromatic amine structures

图式1. 铜催化的芳胺对位C—H键偕二氟烯烃化反应

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

图式2. Ag催化的N,N-二烷基苯胺与炔胺的区域选择性C—H键烯基化反应

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

图式3. 钯催化的苯胺对位C—H键芳基化反应

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

图式4. 钯/铜协同催化的合成稠合色烯并喹啉类化合物

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

图式5. 金催化的咔唑和芳基重氮乙酸甲酯的碳碳偶联反应

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

图式6. CuCl2催化苯胺衍生物的对C—H烷基化反应

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

图式7. Rh催化的芳基乙烯基重氮乙酸酯和芳胺的不对称偶联反应

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

图式8. 铑催化的色烯衍生物的合成

Scheme 8. Rhodium-catalyzed synthesis of chromene derivatives

图式9. 钯和铑的协同催化的全碳季碳中心化合物合成

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

图式10. Rh(II)/Xantphos催化的全碳季碳中心化合物合成

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

图式11. 碱促进钴催化苯胺衍生物的区域和对映选择性对位傅克烷基化反应

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

图式12. 铜催化对的叔烷基卤化物与苯胺的交叉偶联反应

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

图式13. 钌催化的苯胺、烯烃以及α-溴代烷烃的烷基芳基化转化反应

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

图式14. 银催化对亚甲基苯醌与苯胺的区域选择性1,6-氢芳基化反应

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

图式15. 镁催化的苯胺与芳基联烯的对位选择性烯丙基化反应

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

图式16. 铱催化苯胺与芳基炔烃的选择性对位C-烷基化反应

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

图式17. 铱催化的苯胺对位硼酰化反应

Scheme 17. Iridium-catalyzed para-boroylation of anilines

图式18. 铁催化的苯胺对位直接卤化反应

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

图式19. 电催化的芳胺和萘-2-胺衍生物选择性脱氢交叉偶联策略

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

图式20. 通过脱氢交叉偶联的电化学合成对称联苯方案

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

图式21. 电催化三组分反应合成磷硒酸酯

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

图式22. 电化学条件下碘介导的硫代芳基化反应

Scheme 22. Iodine-mediated thioarylation under electrochemical conditions

图式23. 可见光介导钌催化无保护苯胺的对位选择性烷基化反应

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

图式24. 有机光催化的苯胺衍生物和偶氮类化合物的对位选择性偶联

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

图式25. HFIP催化的烯烃氢芳基化反应

Scheme 25. HFIP-catalyzed hydroarylation of olefins

图式26. 酸催化的苯胺与烯烃的(a)三氟甲基芳基化反应(b)芳基化反应

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

图式27. 硼催化1,3-二烯烃与芳胺的氢芳基化反应

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

图式28. B(C6F5)3与HFIP协同催化的双芳基化反应

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

图式29. 结构多样的HFIP基团官能化苯胺衍生物的合成

Scheme 29. Synthesis of structurally diverse HFIP functionalized aniline derivatives

图式30. HFIP促进的苯胺衍生物与芳基乙醛酸水合物的高选择性羟烷基化反应

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

图式31. HFIP介导的三芳基甲烷衍生物合成

Scheme 31. HFIP-mediated synthesis of triarylmethane derivatives

图式32. HFIP介导的1,6-氢芳基化反应实现三芳基甲烷衍生物的合成

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

图式33. 硼烷催化芳胺与苯甲醇的对位和邻位C-烷基化反应

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

图式34. CPA催化苯胺对酮亚胺的对映选择性对位加成反应

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

图式35. CPA催化苯胺对环硫酰亚胺酯的对映选择性对位加成反应

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

图式36. CPA催化的三苯基甲烷的不对称合成

Scheme 36. CPA-catalyzed asymmetric synthesis of triphenylmethanes

图式37. 手性磷酸介导的二苯胺与炔丙基-3-亚甲基吲哚的对位选择性官能化

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

图式38. 咪唑鎓催化的烯丙醇与苯胺偶联反应

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

图式39. Brønsted酸性离子液体催化的双重傅-克反应

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

图式40. 碘催化的苯胺对位硫化反应

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

图式41. 碘/DMSO促进的苯胺选择性芳硫基化反应

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

图式42. 碘介导的咔唑类化合物的选择性C—H硫化反应

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

图式43. H2O/DMSO促进的苯胺对位C—H杂芳基化反应

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

图式44. 苯胺对位溴化反应

Scheme 44. para-Bromination reaction of anilines

参考文献 104

[1]	(a) Lyons T. W.; Sanford M. S. Chem. Rev. 2010, 110, 1147. doi: 10.1021/cr900184e
	(b) Vanjari R.; Singh K. N. Chem. Soc. Rev. 2015, 44, 8062. doi: 10.1039/C5CS00003C
[2]	Sambiagio C.; Schönbauer D.; Blieck R.; Dao-Huy T.; Pototschnig G.; Schaaf P.; Wiesinger T.; Zia M. F.; Wencel-De- lord J.; Besset T.; Maes B. U. W.; Schnürch M. Chem. Soc. Rev. 2018, 47, 6603. doi: 10.1039/c8cs00201k pmid: 30033454
[3]	(a) Engle K. M.; Mei T.-S.; Wasa M.; Yu J.-Q. Acc. Chem. Res. 2012, 45, 788. doi: 10.1021/ar200185g
	(b) Sharma R.; Thakur K.; Kumar R.; Kumar I.; Sharma U. Catal. Rev. 2015, 57, 345. doi: 10.1080/01614940.2015.1058623
	(c) Dutta U.; Maiti S.; Bhattacharya T.; Maiti D. Science 2021, 372, eabd5992.
	(d) Maity S.; Bera A.; Bhattacharjya A.; Maity P. Org. Biomol. Chem. 2023, 21, 5671. doi: 10.1039/D3OB00799E
[4]	(a) Tsukano C. Chem. Pharm. Bull. 2017, 65, 409. doi: 10.1248/cpb.c16-00969
	(b) Cai C.; Zou D. Chin. J. Org. Chem. 2022, 42, 1586 (in Chinese). doi: 10.6023/cjoc202201027
	(蔡晨怡, 邹东, 有机化学, 2022, 42, 1586.) doi: 10.6023/cjoc202201027
	(c) Doraghi F.; Aghanour Ashtiani M. M.; Ameli M.; Larijani B.; Mahdavi M. Chem. Rec. 2024, 24, e202400116. doi: 10.1002/tcr.v24.11
	(d) Liu C.-X.; Yin S.-Y.; Zhao F.; Yang H.; Feng Z.; Gu Q.; You S.-L. Chem. Rev. 2023, 123, 10079. doi: 10.1021/acs.chemrev.3c00149
[5]	(a) Gandeepan P.; Müller T.; Zell D.; Cera G.; Warratz S.; Ackermann L. Chem. Rev. 2019, 119, 2192. doi: 10.1021/acs.chemrev.8b00507
	(b) Su L.; Yu Z.; Ren P.; Luo Z.; Hou W.; Xu H. Org. Biomol. Chem. 2018, 16, 7236. doi: 10.1039/C8OB02071J
	(c) Zhang X.; Bai R.; Xiong H.; Xu H.; Hou W. Bioorg. Med. Chem. Lett. 2020, 30, 126916. doi: 10.1016/j.bmcl.2019.126916
[6]	(a) Zhang J.; Bellomo A.; Creamer A. D.; Dreher S. D.; Walsh P. J. J. Am. Chem. Soc. 2012, 134, 13765. doi: 10.1021/ja3047816
	(b) Bellomo A.; Zhang J.; Trongsiriwat N.; Walsh P. J. Chem. Sci. 2013, 4, 849. doi: 10.1039/C2SC21673F
	(c) Zhang J.; Bellomo A.; Trongsiriwat N.; Jia T.; Carroll P. J.; Dreher S. D.; Tudge M. T.; Yin H.; Robinson J. R.; Schelter E. J.; Walsh P. J. J. Am. Chem. Soc. 2014, 136, 6276. doi: 10.1021/ja411855d
	(d) Cao X.; Sha S.-C.; Li M.; Kim B.-S.; Morgan C.; Huang R.; Yang X.; Walsh P. J. Chem. Sci. 2016, 7, 611. doi: 10.1039/C5SC03704B
	(e) Li J.; Wu C.; Zhou B.; Walsh P. J. J. Org. Chem. 2018, 83, 2993. doi: 10.1021/acs.joc.8b00016
	(f) Li J.; Zou D.; Wang B.; İşcan A.; Jin H.; Chen L.; Zhou F.; Walsh P. J.; Liang G. Org. Chem. Front. 2022, 9, 3854. doi: 10.1039/D2QO00576J
[7]	(a) Yang F.; Zou D.; Chen S.; Wang H.; Zhao Y.; Zhao L.; Li L.; Li J.; Walsh P. J. Adv. Synth. Catal. 2020, 362, 3423 doi: 10.1002/adsc.v362.16
	(b) Zou D.; Gan L.-S.; Yang F.; Wang J.-M.; Li L.-L.; Li J. Tetrahedron Lett. 2020, 61, 152532. doi: 10.1016/j.tetlet.2020.152532
	(c) Wang H.; Mao J.; Shuai S.; Chen S.; Zou D.; Walsh P. J.; Li J. Org. Chem. Front. 2021, 8, 6000. doi: 10.1039/D1QO00944C
[8]	Huang Y.; Zou D. Sci. Sin. Chim. 2023, 53, 932. doi: 10.1360/SSC-2022-0253
[9]	Mary A.; Kanagathara N.; Baby Suganthi A. R. Mater. Proc. 2020, 33, 4751.
[10]	Arıkan C. C.; Kulabaş N.; Küçükgüzel İ. J. Pharmaceut. Biomed. 2023, 223, 115123. doi: 10.1016/j.jpba.2022.115123
[11]	Ni Y.; Liao J.; Qian Z.; Wu C.; Zhang X.; Zhang J.; Xie Y.; Jiang S. Bioorg. Med. Chem. 2022, 53, 116523. doi: 10.1016/j.bmc.2021.116523
[12]	Wang Z.; Wang Y.; Pasangulapati J. P.; Stover K. R.; Liu X.; Schier S.; Weaver D. F. Eur. J. Med. Chem. 2021, 222, 113565. doi: 10.1016/j.ejmech.2021.113565
[13]	Khan S.; Yaqoob M.; Asad M. H. H. B.; Falak R.; Ashraf Z.; Mannan A.; Bukhari S. M.; Alam F.; Rashid U. Future Med. Chem. 2025, 17, 2429. doi: 10.1080/17568919.2025.2561395
[14]	Li J.-F.; Huang R.-Z.; Yao G.-Y.; Ye M.-Y.; Wang H.-S.; Pan Y.-M.; Xiao J.-T. Eur. J. Med. Chem. 2014, 86, 175. doi: 10.1016/j.ejmech.2014.08.003
[15]	(a) Tomkins P.; Gebauer-Henke E.; Leitner W.; Müller T. E. ACS Catal. 2015, 5, 203. doi: 10.1021/cs501122h pmid: 23560824
	(b) Orlandi M.; Brenna D.; Harms R.; Jost S.; Benaglia M. Org. Process Res. Dev. 2018, 22, 430. doi: 10.1021/acs.oprd.6b00205 pmid: 23560824
	(c) Cantillo D.; Moghaddam M. M.; Kappe C. O. J. Org. Chem. 2013, 78, 4530. doi: 10.1021/jo400556g pmid: 23560824
	(d) Zou D.; Wang W.; Hu Y.; Jia T. Org. Biomol. Chem. 2023, 21, 2254. doi: 10.1039/D3OB00064H pmid: 23560824
[16]	(a) Wang X.; Li Y.; Wang M.; Gao Y.; Ma Z.; Lei A.; Li W. Chin. J. Catal. 2025, 72, 392. doi: 10.1016/S1872-2067(25)64658-4
	(b) Popov Y. V.; Mokhov V. M.; Latyshova S. E.; Nebykov D. N.; Panov A. O.; Pletneva M. Y. Russ. J. Gen. Chem. 2017, 87, 2276. doi: 10.1134/S107036321710005X
	(c) Ding Y.; Luo S.; Weng C.; An J. J. Org. Chem. 2019, 84, 15098. doi: 10.1021/acs.joc.9b02056
[17]	(a) Wu J.; Darcel C. ChemCatChem 2022, 14, e202101874. doi: 10.1002/cctc.v14.9
	(b) Doan S. H.; Nguyen T. V. Green Chem. 2022, 24, 7382. doi: 10.1039/D2GC01905A
	(c) Bhunia M.; Sahoo S. R.; Das A.; Ahmed J.; P, S.; Mandal S. K. Chem. Sci. 2020, 11, 1848. doi: 10.1039/C9SC05953A
[18]	Zou D.; Wang W.; Ying J. Adv. Synth. Catal. 2024, 366, 1450. doi: 10.1002/adsc.v366.7
[19]	Zou D.; Ying J. Org. Biomol. Chem. 2025, 10.1039/D5OB01461A.
[20]	Paras N. A.; MacMillan D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. pmid: 12095321
[21]	(a) Leitch J. A.; McMullin C. L.; Paterson A. J.; Mahon M. F.; Bhonoah Y.; Frost C. G. Angew. Chem. Int. Ed. 2017, 56, 15131. doi: 10.1002/anie.201708961 pmid: 28968000
	(b) Tian C.; Wang Q.; Wang X.; An G.; Li G. J. Org. Chem. 2019, 84, 14241. doi: 10.1021/acs.joc.9b01987 pmid: 28968000
	(c) Hu X.; Martin D.; Melaimi M.; Bertrand G. J. Am. Chem. Soc. 2014, 136, 13594. doi: 10.1021/ja507788r pmid: 28968000
	(d) Arun Kumar R.; Srinivasulu A.; Saidulu G.; Santhosh Kumar P.; Sridhar B.; Rajender Reddy K. Tetrahedron 2016, 72, 794. doi: 10.1016/j.tet.2015.12.040 pmid: 28968000
	(e) Bosica G.; Abdilla R. Green Chem. 2017, 19, 5683. doi: 10.1039/C7GC02038D pmid: 28968000
[22]	Brand J. P.; Waser J. Org. Lett. 2012, 14, 744. doi: 10.1021/ol203289v
[23]	Liang S.; Bolte M.; Manolikakes G. Chem.-Eur. J. 2017, 23, 96. doi: 10.1002/chem.v23.1
[24]	Tian C.; Yao X.; Ji W.; Wang Q.; An G.; Li G. Eur. J. Org. Chem. 2018, 2018, 5972. doi: 10.1002/ejoc.v2018.43
[25]	Yin Q.; Klare H. F. T.; Oestreich M. Angew. Chem. Int. Ed. 2016, 55, 3204. doi: 10.1002/anie.v55.9
[26]	Yin Q.; Klare H. F. T.; Oestreich M. Angew. Chem. Int. Ed. 2017, 56, 3712. doi: 10.1002/anie.v56.13
[27]	Doraghi F.; Kalooei Y. M.; Darban N. M. Z.; Larijani B.; Mahdavi M. J. Organomet. Chem. 2024, 1019, 123313. doi: 10.1016/j.jorganchem.2024.123313
[28]	Jacob C.; Annibaletto J.; Maes B. U. W.; Evano G. Synthesis 2023, 55, 1799. doi: 10.1055/a-2039-7985
[29]	(a) Tischler M. O.; Tóth M. B.; Novák Z. Chem. Rec. 2017, 17, 184. doi: 10.1002/tcr.v17.2
	(b) Al Mamari H. H. Reactions 2024, 5, 318. doi: 10.3390/reactions5020016
[30]	(a) Gillis E. P.; Eastman K. J.; Hill M. D.; Donnelly D. J.; Meanwell N. A. J. Med. Chem. 2015, 58, 8315. doi: 10.1021/acs.jmedchem.5b00258 pmid: 26200936
	(b) Meanwell N. A. J. Med. Chem. 2018, 61, 5822. doi: 10.1021/acs.jmedchem.7b01788 pmid: 26200936
[31]	Yang Z.; Pei C.; Koenigs R. M. Org. Lett. 2020, 22, 7234. doi: 10.1021/acs.orglett.0c02568
[32]	Nie X.-D.; Mao Z.-Y.; Guo J.-M.; Si C.-M.; Wei B.-G.; Lin G.-Q. J. Org. Chem. 2022, 87, 2380. doi: 10.1021/acs.joc.1c02263
[33]	(a) Chatupheeraphat A.; Rueping M.; Magre M. Org. Lett. 2019, 21, 9153. doi: 10.1021/acs.orglett.9b03526 pmid: 24437701
	(b) Manikandan R.; Jeganmohan M. Org. Lett. 2014, 16, 912. doi: 10.1021/ol403666s pmid: 24437701
[34]	Lichte D.; Pirkl N.; Heinrich G.; Dutta S.; Goebel J. F.; Koley D.; Gooßen L. J. Angew. Chem. Int. Ed. 2022, 61, e202210009. doi: 10.1002/anie.v61.47
[35]	(a) Chen Y.-L.; Fang K.-C.; Sheu J.-Y.; Hsu S.-L.; Tzeng C.-C. J. Med. Chem. 2001, 44, 2374. pmid: 11428933
	(b) Hegab M. I.; Abdel-Fattah A.-S. M.; Yousef N. M.; Nour H. F.; Mostafa A. M.; Ellithey M. Arch. Pharm. 2007, 340, 396. pmid: 11428933
	(c) Mallick S.; Dutta A.; Ghosh J.; Maiti S.; Mandal A. K.; Banerjee R.; Bandyopadhyay C.; Pal C. Chemotherapy 2011, 57, 388. doi: 10.1159/000330856 pmid: 11428933
	(d) Chib R.; Raut S.; Shah S.; Grobelna B.; Akopova I.; Rich R.; Sørensen T. J.; Laursen B. W.; Grajek H.; Gryczynski Z.; Gryczynski I. Dyes Pigm. 2015, 117, 16. doi: 10.1016/j.dyepig.2015.01.027 pmid: 11428933
[36]	Shen G.; Wang Z.; Huang X.; Hong M.; Fan S.; Lv X. Org. Lett. 2020, 22, 8860. doi: 10.1021/acs.orglett.0c03229
[37]	Jana S.; Empel C.; Pei C.; Aseeva P.; Nguyen T. V.; Koenigs R. M. ACS Catal. 2020, 10, 9925. doi: 10.1021/acscatal.0c02230
[38]	(a) Arredondo V.; Hiew S. C.; Gutman E. S.; Premachandra I. D. U. A.; Van Vranken D. L. Angew. Chem. Int. Ed. 2017, 56, 4156. doi: 10.1002/anie.201611845 pmid: 28295890
	(b) Shen H.-Q.; Wu B.; Xie H.-P.; Zhou Y.-G. Org. Lett. 2019, 21, 2712. doi: 10.1021/acs.orglett.9b00687 pmid: 28295890
	(c) Shen H.-Q.; Xie H.-P.; Sun L.; Zhou Y.-G. Organometallics 2019, 38, 3902. doi: 10.1021/acs.organomet.9b00219 pmid: 28295890
[39]	Gao L.; Liu S.; Wang Z.-C.; Mao Y.; Shi S.-L. Asian J. Org. Chem. 2022, 11, e202100723. doi: 10.1002/ajoc.v11.2
[40]	Zhu D.-X.; Xia H.; Liu J.-G.; Chung L. W.; Xu M.-H. J. Am. Chem. Soc. 2021, 143, 2608. doi: 10.1021/jacs.0c13191
[41]	(a) Chen D.; Zhang X.; Qi W.-Y.; Xu B.; Xu M.-H. J. Am. Chem. Soc. 2015, 137, 5268. doi: 10.1021/jacs.5b00892
	(b) Chen D.; Zhu D.-X.; Xu M.-H. J. Am. Chem. Soc. 2016, 138, 1498. doi: 10.1021/jacs.5b12960
[42]	Li Z.-Y.; Zhang J.-P.; Ying Y.-Y.; Yan D.; Jiao L.; Hao E. Org. Lett. 2022, 24, 7888. doi: 10.1021/acs.orglett.2c02853
[43]	Akritopoulou-Zanze I.; Patel J. R.; Hartandi K.; Brenneman J.; Winn M.; Pratt J. K.; Grynfarb M.; Goos-Nisson A.; von Gel- dern T. W.; Kym P. R. Bioorg. Med. Chem. Lett. 2004, 14, 2079. pmid: 15080982
[44]	Zhang F.-L.; Hong K.; Li T.-J.; Park H.; Yu J.-Q. Science 2016, 351, 252. doi: 10.1126/science.aad7893
[45]	(a) Rej S.; Chatani N. J. Am. Chem. Soc. 2021, 143, 2920. doi: 10.1021/jacs.0c13013
	(b) Song H.; Li Y.; Yao Q.-J.; Jin L.; Liu L.; Liu Y.-H.; Shi B.-F. Angew. Chem. Int. Ed. 2020, 59, 6576. doi: 10.1002/anie.v59.16
[46]	Chen Q.; Huang T.; Shao Y.; Tang S.; Sun J. J. Org. Chem. 2023, 88, 3308. doi: 10.1021/acs.joc.2c02730
[47]	Ge Z.; Lu B.; Teng H.; Wang X. Chem.-Eur. J. 2023, 29, e202202820. doi: 10.1002/chem.v29.3
[48]	Zhou J.; Li Z.-H.; Wang L.; Kang J.-C.; Wang X.-H.; Zhang S.-Y. Org. Lett. 2021, 23, 9353. doi: 10.1021/acs.orglett.1c03399 pmid: 34874735
[49]	Choi S.; Choi Y.; Kim Y.; Lee J.; Lee S. Y. J. Am. Chem. Soc. 2023, 145, 24897.
[50]	Wang X.-J.; Cheng Y.-H.; Lv X.-Y.; Liang L.-Y.; An G.-H.; Li G.-M. Chin. Chem. Lett. 2025, doi: https://doi.org/10.1016/j.cclet.2025.112154.
[51]	Xiong B.; Xu S.; Xu W.; Liu Y.; Zhang L.; Tang K.-W.; Yin S.-F.; Wong W.-Y. Org. Chem. Front. 2022, 9, 3807. doi: 10.1039/D2QO00541G
[52]	Ghosh S.; Saha S. N.; Baidya M. Org. Lett. 2023, 25, 5073. doi: 10.1021/acs.orglett.3c01764
[53]	Luo R.; Liang Y.; Wang S.; Liao J.; Ouyang L. J. Catal. 2023, 428, 115184. doi: 10.1016/j.jcat.2023.115184
[54]	Yuan C.; Zhang W.; Zang W.; Zhu L.; Yu Y.; Han X. Org. Lett. 2025, 27, 13299. doi: 10.1021/acs.orglett.5c04333
[55]	(a) Montero Bastidas J. R.; Oleskey T. J.; Miller S. L.; Smith M. R., III; Maleczka, R. E., Jr. J. Am. Chem. Soc. 2019, 141, 15483. doi: 10.1021/jacs.9b08464 pmid: 31525037
	(b) Mihai M. T.; Williams B. D.; Phipps R. J. J. Am. Chem. Soc. 2019, 141, 15477. doi: 10.1021/jacs.9b07267 pmid: 31525037
[56]	Haldar C.; Bisht R.; Chaturvedi J.; Guria S.; Hassan M. M. M.; Ram B.; Chattopadhyay B. Org. Lett. 2022, 24, 8147. doi: 10.1021/acs.orglett.2c03188
[57]	Tanemura K. Tetrahedron 2025, 176, 134544. doi: 10.1016/j.tet.2025.134544
[58]	(a) Yuan Y.; Cao Y.; Qiao J.; Lin Y.; Jiang X.; Weng Y.; Tang S.; Lei A. Chin. J. Chem. 2019, 37, 49. doi: 10.1002/cjoc.v37.1
	(b) Hua J.; Fang Z.; Xu J.; Bian M.; Liu C.; He W.; Zhu N.; Yang Z.; Guo K. Green Chem. 2019, 21, 4706. doi: 10.1039/C9GC02131K
	(c) Zhao Z.; Yan H.; Zhou Y.; Xue W.; Gu L.; Zhang S. Chin. J. Chem. 2024, 42, 2049. doi: 10.1002/cjoc.v42.17
	(d) Zhang C.; Han Z.; Zhao Z.; Zhou Y.; Gu L. Org. Lett. 2025, 27, 9121. doi: 10.1021/acs.orglett.5c02295
[59]	Luo M.-J.; Li Y.; Ouyang X.-H.; Li J.-H.; He D.-L. Chem. Commun. 2020, 56, 2707. doi: 10.1039/C9CC09879H
[60]	(a) Matsumoto K.; Yoshida M.; Shindo M. Angew. Chem. Int. Ed. 2016, 55, 5272. doi: 10.1002/anie.201600400 pmid: 31464136
	(b) Matsumoto K.; Takeda S.; Hirokane T.; Yoshida M. Org. Lett. 2019, 21, 7279. doi: 10.1021/acs.orglett.9b02527 pmid: 31464136
[61]	Liu X.; Cai T.-C.; Guo D.; Wang B.-B.; Ying S.; Wang H.; Tang S.; Shen Q.; Gui Q.-W. Tetrahedron Lett. 2021, 70, 153021. doi: 10.1016/j.tetlet.2021.153021
[62]	Zhang C.; Zhou Y.; Zhao Z.; Xue W.; Gu L. Chem. Commun. 2022, 58, 13951. doi: 10.1039/D2CC05570H
[63]	Yu J.; Li T.; Sun Q.; Wang Z. RSC Adv. 2025, 15, 12042. doi: 10.1039/D5RA00100E
[64]	Lv X.; Cheng Y.; Zong Y.; Wang Q.; An G.; Wang J.; Li G. ACS Catal. 2023, 13, 7310. doi: 10.1021/acscatal.3c00901
[65]	(a) Cheng Y.; He Y.; Zheng J.; Yang H.; Liu J.; An G.; Li G. Chin. Chem. Lett. 2021, 32, 1437. doi: 10.1016/j.cclet.2020.09.044
	(b) Fan W.-T.; Li Y.; Wang D.; Ji S.-J.; Zhao Y. J. Am. Chem. Soc. 2020, 142, 20524. doi: 10.1021/jacs.0c09545
[66]	Cheng Y.; Zhang X.; An G.; Li G.; Yang Z. Chin. Chem. Lett. 2023, 34, 107625. doi: 10.1016/j.cclet.2022.06.048
[67]	Das B.; Sahoo S. R.; Das A.; Pathak B.; Sarkar D. Org. Lett. 2023, 25, 7733. doi: 10.1021/acs.orglett.3c03137
[68]	Liu R.; Tong H. E.; Li Y.; Shi W.-Y.; Guo H.; Zhou R. J. Org. Chem. 2025, 90, 17140. doi: 10.1021/acs.joc.5c02448
[69]	Jiang Y.; Li B.; Ma N.; Shu S.; Chen Y.; Yang S.; Huang Z.; Shi D.; Zhao Y. Angew. Chem. Int. Ed. 2021, 60, 19030. doi: 10.1002/anie.v60.35
[70]	Motiwala H. F.; Fehl C.; Li S.-W.; Hirt E.; Porubsky P.; Aubé J. J. Am. Chem. Soc. 2013, 135, 9000. doi: 10.1021/ja402848c pmid: 23687993
[71]	Tian Y.; Xu X.; Zhang L.; Qu J. Org. Lett. 2016, 18, 268. doi: 10.1021/acs.orglett.5b03438 pmid: 26739256
[72]	Zhu Y.; Colomer I.; Thompson A. L.; Donohoe T. J. J. Am. Chem. Soc. 2019, 141, 6489. doi: 10.1021/jacs.9b02198
[73]	Champagne P. A.; Benhassine Y.; Desroches J.; Paquin J.-F. Angew. Chem. Int. Ed. 2014, 53, 13835. doi: 10.1002/anie.v53.50
[74]	Nielsen C. D. T.; White A. J. P.; Sale D.; Bures J.; Spivey A. C. J. Org. Chem. 2019, 84, 14965. doi: 10.1021/acs.joc.9b02393
[75]	Colomer I. ACS Catal. 2020, 10, 6023. doi: 10.1021/acscatal.0c00872
[76]	Corral Suarez C.; Colomer I. Chem. Sci. 2023, 14, 12083. doi: 10.1039/D3SC03868H
[77]	Winfrey L.; Yun L.; Passeri G.; Suntharalingam K.; Pulis A. P. Chem.-Eur. J. 2024, 30, e202303130. doi: 10.1002/chem.v30.13
[78]	Kumar G.; Qu Z.-W.; Grimme S.; Chatterjee I. Org. Lett. 2021, 23, 8952. doi: 10.1021/acs.orglett.1c03457
[79]	Li X.; Zhu Y.; Gong Z.; Li J.; Xie J.; Zhao Z.; Li J.; Jia C. Green Chem. 2024, 26, 10969. doi: 10.1039/D4GC03917C
[80]	(a) Li L.; Liu J.; Zhu L.; Cutler S.; Hasegawa H.; Shan B.; Medina J. C. Bioorg. Med. Chem. Lett. 2006, 16, 1638. doi: 10.1016/j.bmcl.2005.12.015 pmid: 30034593
	(b) Cheng J.-F.; Chen M.; Wallace D.; Tith S.; Haramura M.; Liu B.; Mak C. C.; Arrhenius T.; Reily S.; Brown S.; Thorn V.; Harmon C.; Barr R.; Dyck J. R. B.; Lopaschuk G. D.; Nadzan A. M. J. Med. Chem. 2006, 49, 1517. doi: 10.1021/jm050109n pmid: 30034593
	(c) Nishiyama Y.; Mori S.; Makishima M.; Fujii S.; Kagechika H.; Hashimoto Y.; Ishikawa M. ACS Med. Chem. Lett. 2018, 9, 641. doi: 10.1021/acsmedchemlett.8b00058 pmid: 30034593
[81]	Li X.; Wu Y.; Li J.; Xie J.; Liu J.; Wen Z.; Zhao Z.; Jia C. Green Chem. 2025, 27, 7234. doi: 10.1039/D5GC00878F
[82]	Yang J.; Liu S.; Gui J.; Xiong D.; Li J.; Wang Z.; Ren J. J. Org. Chem. 2022, 87, 6352. doi: 10.1021/acs.joc.1c03155
[83]	Teli Y. A.; Reetu R.; Chanu S. A.; Kant K.; Keremane K. S.; Almeer R.; Singh V.; Malakar C. C. Chem Asian J. 2024, 19, e202400635. doi: 10.1002/asia.v19.21
[84]	Teli Y. A.; Reetu R.; Gujjarappa R.; Banerjee S.; Ghanta S.; Patel M. J.; Singh V.; Al-Zaqri N.; Sengupta R.; Malakar C. C. Eur. J. Org. Chem. 2024, 27, e202301086. doi: 10.1002/ejoc.v27.7
[85]	Zhu L.; Ren Y.; Liu X.; Xu S.; Li T.; Xu W.; Li Z.; Liu Y.; Xiong B. Chem Asian J. 2023, 18, e202300792. doi: 10.1002/asia.v18.23
[86]	Huang P.; Jiang X.; Gao D.; Wang C.; Shi D.-Q.; Zhao Y. Org. Chem. Front. 2023, 10, 2476. doi: 10.1039/D3QO00342F
[87]	Hu H.-L.; Chen P.; Niu Y.-D.; Li M.-Y.; Shi J.; Jiang Y.-J. Synlett 2024, 36, 739. doi: 10.1055/a-2404-2285
[88]	(a) Bai H.-Y.; Tan F.-X.; Liu T.-Q.; Zhu G.-D.; Tian J.-M.; Ding T.-M.; Chen Z.-M.; Zhang S.-Y. Nat. Commun. 2019, 10, 3063. doi: 10.1038/s41467-019-10858-x
	(b) Akiyama T.; Itoh J.; Yokota K.; Fuchibe K. Angew. Chem. Int. Ed. 2004, 43, 1566. doi: 10.1002/anie.v43:12
[89]	Liu C.; Tan F.-X.; Zhou J.; Bai H.-Y.; Ding T.-M.; Zhu G.-D.; Zhang S.-Y. Org. Lett. 2020, 22, 2173. doi: 10.1021/acs.orglett.0c00262
[90]	Li Z.-H.; Zhou J.; Liu C.; Tan F.-X.; Wang L.; Zhu G.-D.; Zhang S.-Y. Chem Catal. 2024, 4, 100918.
[91]	Zhang M.; Qu X.-Y.; Li R.-R.; Lin B.; Liu X.-L.; Zhao J.-Q. J. Org. Chem. 2025, 90, 10702. doi: 10.1021/acs.joc.5c00929
[92]	Zhang R.-L.; Liu B.; Qiu K.-X.; Li H.-T.; Zhang H.-N.; Shen B.-C.; Sun Z.-W. Org. Lett. 2023, 25, 1711. doi: 10.1021/acs.orglett.3c00370
[93]	Parida C.; Granda J. M. Org. Lett. 2025, 27, 12807. doi: 10.1021/acs.orglett.5c04100
[94]	Albert-Soriano M.; Hernández-Martínez L.; Pastor I. M. ACS Sustainable Chem. Eng. 2018, 6, 14063. doi: 10.1021/acssuschemeng.8b02614
[95]	Gisbert P.; Albert-Soriano M.; Pastor I. M. Eur. J. Org. Chem. 2019, 2019, 4928. doi: 10.1002/ejoc.v2019.30
[96]	Albert-Soriano M.; M. Pastor I. Adv. Synth. Catal. 2020, 362, 2494. doi: 10.1002/adsc.v362.12
[97]	Ponpao N.; Senapak W.; Saeeng R.; Jaratjaroonphong J.; Sirion U. RSC Adv. 2021, 11, 22692. doi: 10.1039/D1RA03724B
[98]	Jiang X.; Shen Z.; Zheng C.; Fang L.; Chen K.; Yu C. Tetrahedron Lett. 2020, 61, 152141. doi: 10.1016/j.tetlet.2020.152141
[99]	(a) Yang D.; Yan K.; Wei W.; Zhao J.; Zhang M.; Sheng X.; Li G.; Lu S.; Wang H. J. Org. Chem. 2015, 80, 6083. doi: 10.1021/acs.joc.5b00540
	(b) Wang H.-H.; Shi T.; Gao W.-W.; Wang Y.-Q.; Li J.-F.; Jiang Y.; Hou Y. S.; Chen C.; Peng X.; Wang Z. Chem. Asian J. 2017, 12, 2675. doi: 10.1002/asia.v12.20
[100]	Zhao W.; Zhang F.; Deng G.-J. J. Org. Chem. 2021, 86, 291. doi: 10.1021/acs.joc.0c02078
[101]	Das M.; Kumar V.; Venkatesh C.; Gandeepan P. J. Org. Chem. 2025, 90, 16470. doi: 10.1021/acs.joc.5c01976
[102]	Xu J.; Huang L.; He L.; Liang C.; Ouyang Y.; Shen J.; Jiang M.; Li W. Green Chem. 2021, 23, 6632. doi: 10.1039/D1GC01899J
[103]	Bovonsombat P.; Hocks A.; Kittithanaluk P.; We J. T.; Khanthapura P.; Choosakoonkriang S.; Srikamhom N.; Ploymanee F. ChemistrySelect 2025, 10, e202500544.
[104]	Zhou Y.; Jones A. M. Molecules 2024, 29, 1445. doi: 10.3390/molecules29071445

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

RichHTML

PDF

可视化

摘要/Abstract

引用此文

分享此文

图/表 45

参考文献 104

相关文章 15

编辑推荐

相关统计

本文评价

[1]	许颖, 杨美琳, 崔大鹏, 于淼, 刘颖杰. 脱氟反应的研究进展[J]. 有机化学, 2026, 46(5): 1962-1983.
[2]	赵子鸣, 郑剑峰, 黄培强. 光催化的由亚胺合成胺的研究进展[J]. 有机化学, 2026, 46(5): 1984-2001.
[3]	程熹, 李雅琳, 吴鹏, 苏敏, 张梓轩, 焦民均, 刘雪粉, 罗书平. 蒽醌光敏剂设计合成与光催化C(sp³)—H氧化反应性能研究[J]. 有机化学, 2026, 46(5): 2104-2111.
[4]	廖云, 唐丽娟, 宗映彤, 于道鸿. 钌催化C(sp²)—H键的不对称官能化研究进展[J]. 有机化学, 2026, 46(5): 1795-1812.
[5]	白燕茹, 周来运, 刘广华, 王青. 有机大共轭分子C—H亲核取代反应的研究进展[J]. 有机化学, 2026, 46(5): 1883-1896.
[6]	侯馨怡, 史同同, 李泽江, 董庆昊, 孙凯, 王薪. 可见光诱导的磷酰化环化合成磷酰基取代的吲哚并二氮䓬[J]. 有机化学, 2026, 46(4): 1776-1787.
[7]	郑婧斐, 吕琪妍, 孙凯, 陈晓岚, 屈凌波, 王金泉, 於兵. 自由基介导的6-氮杂尿嘧啶官能团化研究进展[J]. 有机化学, 2026, 46(4): 1603-1620.
[8]	赵雨晴, 朱先进, 石凌宇, 魏鸣宇, 徐紫涵, 石永佳, 李旭锋, 杨道山. 环硫鎓盐开环官能化反应的研究进展[J]. 有机化学, 2026, 46(4): 1572-1602.
[9]	张皓然, 贾均松, 俞琼, 吴宇, 李玉龙, 舒伟. 可见光催化烯烃的氢胺化和氢(磺)酰胺化反应[J]. 有机化学, 2026, 46(4): 1166-1180.
[10]	杨珊, 陈亚苏, 朱晨. 自由基介导的官能团迁移-环化构建含氮稠杂芳烃[J]. 有机化学, 2026, 46(4): 1739-1749.
[11]	叶富, 袁伟明. 光氧化还原催化炔烃的双碳官能团化反应进展[J]. 有机化学, 2026, 46(4): 1146-1165.
[12]	卢琳玉, 亓雨彤, 张庭珲, 金胜男, 曹中艳, 张洪伟. 自由基介导烯烃的1,2,n-三官能团化反应研究进展[J]. 有机化学, 2026, 46(4): 1540-1559.
[13]	董建洋, 薛东. 自由基途径的[1.1.1]螺桨烷官能化研究进展[J]. 有机化学, 2026, 46(4): 1464-1480.
[14]	孟令旭, 申霖, 罗祥玲, 林玉妹, 龚磊. 具有光活性的铬、钴配合物的设计及其在有机合成中的应用进展[J]. 有机化学, 2026, 46(4): 1513-1528.
[15]	苏雯鑫, 崔浩, 张霄. 单质硫(S₈)参与的光化学反应研究进展[J]. 有机化学, 2026, 46(4): 1360-1375.