SIOC English
有机化学
高级检索

有机化学 >

0 202604030

DOI: https://doi.org/10.6023/cjoc202604030

红光介导有机合成反应

  • 张令红 ,
  • 孔慢慢 ,
  • 张曌霞 ,
  • 江智勇
展开
  • a兰州文理学院化工学院 甘肃兰州 730000;
    b河南师范大学化学化工学院 河南新乡 453007

收稿日期: 2026-04-21

  修回日期: 2026-06-10

  网络出版日期: 2026-07-24

基金资助

国家自然科学基金(No. 22171072, 21925103)资助项目; 兰州文理学院引进博士科研启动经费(2025BSQD17)资助项目.

收起

Red Light-Mediated Organic Synthesis Reactions

  • Zhang Linghong ,
  • Kong Manman ,
  • Zhaoxia Zhang ,
  • Jiang Zhiyong
Expand
  • aSchool of Chemical Engineering, Lanzhou University of Arts and Science, LanZhou, Gansu 730000;
    bSchool of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007

Received date: 2026-04-21

  Revised date: 2026-06-10

  Online published: 2026-07-24

Supported by

National Natural Science Foundation of China (Nos. 22171072, 21925103)

Fold

摘要

光化学领域的迅猛发展为可见光介导的有机合成带来了诸多技术突破, 其中红光因具有波长较长、光子能量较低、对生物体系损伤小且反应副产物少的独特优势, 已成为该领域的研究热点之一. 与传统紫外光及蓝光催化体系相比, 红光催化能够以更温和的方式实现有机反应的高效可控进行, 有效规避非特异性副反应的发生. 基于此, 本文系统梳理了近年来红光介导有机合成反应的研究进展, 依据反应的核心作用机理, 将其划分为单电子转移、能量转移、金属键均裂、底物直接激发及光酶催化五大类型, 并对各类反应的具体反应路径、调控规律及核心作用机理展开系统阐述与深入探讨, 为红光介导有机合成的后续研究与应用提供理论参考和研究思路.

关键词： 红光; 有机合成; 自由基; 反应机理

本文引用格式

张令红 , 孔慢慢 , 张曌霞 , 江智勇 . 红光介导有机合成反应[J]. 有机化学, 0 : 202604030 . DOI: 10.6023/cjoc202604030

Abstract

The rapid advancement of photochemistry has enabled significant technological breakthroughs in visible light-mediated organic synthesis. Within this progress, red light has emerged as a focal area of research due to its distinctive photophysical and biological advantages: longer wavelength, lower photon energy, minimal phototoxicity toward biological systems, and reduced generation of undesired side products. Compared with conventional ultraviolet (UV) and blue light-driven catalytic systems, red light-mediated catalysis permits efficient and selective organic transformations under mild reaction conditions, thereby suppressing non-specific side reactions and enhancing synthetic control. In this review, we systematically survey recent developments in red light-driven organic synthesis. Reactions are classified into five mechanistic categories: single-electron transfer (SET), energy transfer (EnT), metal-ligand bond homolysis, direct substrate excitation, and photoenzymatic catalysis. For each category, we provide a rigorous analysis of representative transformations, key operational parameters governing selectivity and efficiency, and current mechanistic understanding. Collectively, this work offers a consolidated conceptual framework and identifies promising avenues for future investigation and practical implementation of red light-enabled synthetic methodologies.

Key words： red light; organic synthesis; radical; reaction mechanism

参考文献

[1] (a) Prier C. K.; Rankic D. A.; MacMillan, D. W. C. Chem. Rev.,2013, 113, 5322.
(b) Romero N. A.; Nicewicz, D. A. Chem. Rev.,2016, 116, 10075.
(c) Yin Y. L.; You M. D.; Li X. T.; Jiang, Z. Y. Chem. Soc. Rev.,2025, 54, 2246.
[2] Skubi K.L.; Blum T.R.; Yoon T.P. Chem. Rev.,2016, 116, 10035.
[3] Ham W. T.; Mueller H. A.; Sliney D. H. Nature,1976, 260, 153.
[4] Smith A. M.; Mancini M. C.; Nie S. Nat. Nanotechnol.,2009, 4, 710.
[5] Szaciłowski K.; Macyk W.; Drzewiecka-Matuszek A.; Brindel M.; Stochell G. Chem. Rev.,2005, 105, 2647.
[6] (a) Sellet N.; Cormier M.; Goddard, J.-P. Org. Chem. Front.,2021, 8, 6783.
(b) Connell, T. U. Dalton. Trans., 2022, 51, 13176.
[7] (a) Schade A. H.; Mei, L. Org. Biomol. Chem.,2023, 21, 2472.
(b) Huang L.; Han G.Nat. Rev. Chem.,2024, 8, 238.
(c) Zhong M.; Sun Y. Chem. Catal.,2024, 4, 100973.
(d) Fortier L.; Lefebvre C.; Hoffmann, N. Beilstein. J. Org. Chem.,2025, 21, 296.
(e) Zhang T.; Pradhan S.; Das, S. Angew. Chem. Int. Ed. Engl.,2025, 64(30): e202501194.
(f) Cabanero D. C.; Rovis, T. Nat. Rev. Chem.,2025, 9, 28.
[8] Lee J.; Papatzimas J. W.; Bromby A. D.; Gorobets E.; Derksen, D. J. RSC. Adv.,2016, 6, 59269.
[9] Yerien D. E.; Cooke M. V.; Garcia-Vior M. C.; Barata-Vallejo S.; Postigo, A. Org. Biomol. Chem.,2019, 17, 3741.
[10] (a) Cocquet G.; Ferroud C.; Guy A. Tetrahedron,2000, 56, 2975.
(b) Cocquet G.; Ferroud C.; Simon P.; Taberna, P.-L. JCS. PERKIN. II.,2000, 6, 1147.
[11] Mei L.; Veleta J. M.; Gianetti, T. L. J. Am. Chem. Soc.,2020, 142, 12056.
[12] Buksh B. F.; Knutson S. D.; Oakley J. V.; Bissonnette N. B.; Oblinsky D. G.; Schwoerer M. P.; Seath C. P.; Geri J. B.; Rodriguez-Rivera F. P.; Parker D. L.; Scholes G. D.; Ploss A.; MacMillan, D. W. C. J. Am. Chem. Soc.,2022, 144, 6154.
[13] Gianetti T. L.; Stull S. M.; Mei L. Synlett,2021, 33, 1194.
[14] Goldschmid S. L.; Soon Tay N. E.; Joe C. L.; Lainhart B. C.; Sherwood T. C.; Simmons E. M.; Sezen-Edmonds M.; Rovis, T. J. Am. Chem. Soc.,2022, 144, 22409.
[15] Orlowska K.; Luczak K.; Krajewski P.; Santiago J. V.; Rybicka-Jasinska K.; Gryko D. Chem. Commun.,2023, 59, 14649.
[16] Liu M.Y.; Luo Y.l.; Yan J.Y.; Xiong X.L.; Xing X.W.; Kim J. S.; Zou, T.T. J. Am. Chem. Soc.,2023, 145, 10082.
[17] Zhang T.; Rabeah J.; Das S. Nat. Commun.,2024, 15, 5208.
[18] Hossain M. M., Shaikh A. C., Kaur R., Gianetti, T. L. J. Am. Chem. Soc.,2024, 146, 7922.
[19] Lal N.; Deepshikha; Singh P.; Shaikh, A. C. Chem. Commun.,2025, 61, 3005.
[20] Sun Y. J.; Song G. Y.; Yan Y. G.; Kang T. F.; Dong J. Y.; Li G.; Xue D. Green. Chem.,2025, 27, 5315.
[21] Wang C. Y.; Dong J. Y.; Sun Y. J.; Li T.; Kang T. F.; Xue D. Org. Lett.,2025, 27, 14193.
[22] Montoto D.; Deus-Lorenzo U.; Tomas-Gamasa M.; Mascareñas J. L.; Mato, M. Org. Biomol. Chem.,2025, 23, 9833.
[23] Deus-Lorenzo U.; Di Forti R.; Cadranel A.; Tomas-Gamasa M.; Mascareñas J. L.; Mato M. Org. Lett.,2026, 28, 5508.
[24] Yan X.S.; Zhao J. H.; Wang Q.; Wang W.J.; Ding Y.C.; Zhou Y.T.; Chen G.; Du J.J.; Huang W.R.; Chu, L. J. Am. Chem. Soc.,2025, 147, 20957.
[25] Mato M.; Rivas-Saborido A.; Casas-Pais A.; Tomas-Gamasa M.; Mascareñas, J. L. J. Am. Chem. Soc.,2026, 148, 5946.
[26] Mei L.; Moutet J.; Stull S. M.; Gianetti, T. L. J. Org. Chem.,2021, 86, 10640.
[27] Ishikawa Y.; Kameyama T.; Torimoto T.; Maeda H.; Segi M.; Furuyama T. Chem. Commun.,2021, 57, 13594.
[28] Tay N. E. S.; Ryu K. A.; Weber J. L.; Olow A. K.; Cabanero D. C.; Reichman D. R.; Oslund R. C.; Fadeyi O. O.; Rovis T. Nat. Chem.,2023, 15, 101.
[29] Ogbu I. M.; Bassani D. M.; Robert F.; Landais Y. Chem. Commun.,2022, 58, 8802.
[30] Yan P.; Zeng, Rong, Bao B.; Yang X. M.; Zhu L.; Pan B.; Niu S. L.; Qi X. W.; Li Y. L.; Ouyang Q. Green. Chem.,2022, 24, 9263.
[31] Cabanero D. C.; Nguyen J. A.; Cazin C. S. J.; Nolan S. P.; Rovis T. ACS. Catal.,2023, 13, 4384.
[32] Okanishi Y.; Takemoto O.; Kawahara S.; Hayashi S.; Takanami T.; Yoshimitsu T. Org. Lett.,2024, 26, 3929.
[33] Kai U.; Katsurayama Y.; Nishida R.; Kameyama T.; Torimoto T.; Furuyama, T. J. Org. Chem.,2024, 89, 8178.
[34] Miyamoto Y.; Muraoka K.; Murakami S.; Matsudaira T.; Ohmiya, H. J. Am. Chem. Soc.,2025, 147, 41185.
[35] Muraoka K.; Miyamoto Y.; Murakami S.; Ohmiya H.ACS. Catal., 2026. (正式页码未出)
[36] Gizatullin A.; Yuan T.T.; Grotjahn S.; Cavallo L.; Konig B.; Zhu C.; Rueping, M. Angew. Chem. Int. Ed. Engl.,2026, 65, e26086.
[37] Schlau-Cohen Gabriela S.R. C.; Kitzmann W. R.; Heinze K.; de Oliveira K. T.; Opatz, T. J. Org. Chem.,2022, 87, 5630.
[38] Grundke C.; Silva, Cesana Paul T.; Li B. X.; Shepard S. G.; Ting S. I.; Hart S. M.; Olson C. M.; Martinez Alvarado J. I.; Son M. J.; Steiman T. J.; Castellano F. N.; Doyle Abigail G.; MacMillan D. W. C.; Schlau-Cohen G. S. Chem.,2022, 8, 174.
[39] Yamamoto H.; Yamaoka, K., Shinohara A.; Shibata K.; Takao K. I.; Ogura A. Chem. Sci.,2023, 14, 11243.
[40] Cabanero D. C.; Kariofillis S. K.; Johns A. C.; Kim J.; Ni J.; Park S.; Parker, D. L. Jr.; Ramil C. P.; Roy X.; Shah N. H.; Rovis, T. J. Am. Chem. Soc.,2024, 146, 1337.
[41] Watanabe K.; Takada I.; Yamamoto R.; Kobashi H.; Maki K.; Nomura N.; Sasada R.; Tai I.; China H.; Niwa T.; Hosoya T.; Kitagishi H.; Negi S.; Kodera M.; Yamamoto, Y. J. Am. Chem. Soc.,2026, 148, 16039.
[42] Su X. D.; Liu Q.; Cheng J. T.; Wang Z. X.; Chen, X. Y. Org. Lett.,2024, 26, 7976.
[43] Su X. D.; Li X. N.; Liu Q.; Yang Z. S.; Wang Z. X.; Chen, X. Y. Org. Lett.,2025, 27, 3043.
[44] Ogura A.; Ichii N.; Shibata K.; Takao, K.-i. Bull. Chem. Soc. Jpn.,2020, 93, 936.
[45] Mato M.; Bruzzese P. C.; Takahashi F.; Leutzsch M.; Reijerse E. J.; Schnegg A.; Cornella, J. Am. Chem. Soc.,2023, 145, 18742.
[46] Giraldi V.; Marchini M.; Di Giosia M.; Gualandi A.; Cirillo M.; Calvaresi M.; Ceroni P.; Giacomini D.; Cozzi, P. G. New. J. Chem,2022, 46, 8662.
[47] Carceller J. M.; Jayee B.; Page C. G.; Oblinsky D. G.; Mondragón-Solórzano G.; Chintala N.; Cao J. Z.; Alassad Z.; Zhang Z.; Y; White N.; Diaz D. J.; Ellington A. D.; Scholes G. D.; Dong S.-S.; Hyster T. K. Chem.,2025, 11, 102318
[48] Zhao Z.; Li J.; Yuan W.; Cheng D.; Ma S.; Li Y. F.; Shi Z. J.; Hu, K. J. Am. Chem. Soc.,2024, 146,1364.
Options
文章导航

/

〈 〉