Citation: Hefei Yang, Le-Cheng Wang, Xiao-Feng Wu. Sustainable carbonylative transformation of alkyl iodides to amides via crosslinking of EDA and XAT[J]. Chinese Chemical Letters, ;2025, 36(9): 110843. doi: 10.1016/j.cclet.2025.110843 shu

Sustainable carbonylative transformation of alkyl iodides to amides via crosslinking of EDA and XAT

Hefei Yang ^{a, b} ,
Le-Cheng Wang ^{a, b} ,
Xiao-Feng Wu ^{a, b, *,}

a.
Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
b.
Leibniz-Institut für Katalyse e.V., Rostock 18059, Germany

Xiao-Feng.Wu@catalysis.de

Received Date: 13 November 2024
Revised Date: 1 January 2025
Accepted Date: 10 January 2025
Available Online: 11 January 2025

Figures(6)

The amide moiety plays an important role as a powerful bioactive backbone, and as the synthetic chemistry community moves toward more sp³-rich scaffolds, alkyl halides have become the feedstock of choice for obtaining carbonylation products. With the development of photoredox catalysis, several aminocarbonylation systems for alkyl halides were developed which usually require transition metal catalysis. Considering the demands for green sustainable chemical synthesis, here we report a metal-free, exogenous catalyst-free aminocarbonylation reaction of alkyl iodides under atmospheric pressure of carbon monoxide. Through a combination of EDA and XAT strategies, the reaction occurs efficiently under only light irradiation at room temperature.
- Carbonylation,
- Amide,
- Metal-free,
- Phtotchemistry,
- Radical
1. [1]
  U. Boas, J. Brask, K.J. Jensen, Chem. Rev. 109 (2009) 2092–2118. doi: 10.1021/cr068206r
2. [2]
  A. Brennführer, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 48 (2009) 4114–4133. doi: 10.1002/anie.200900013
3. [3]
  I. Ziccarelli, R. Mancuso, F. Giacalone, et al., J. Catal. 413 (2022) 1098–1110. doi: 10.1016/j.jcat.2022.08.007
4. [4]
  M. Yang, Y. Liu, X. Qi, Y. Zhao, X.F. Wu, Green Synth. Catal. 5 (2024) 211–269.
5. [5]
  R.J. Atkins, A. Banks, R.K. Bellingham, et al., Org. Process Res. Dev. 7 (2003) 663–675. doi: 10.1021/op034023k
6. [6]
  C.F.J. Barnard, Organometallics. 27 (2008) 5402–5422. doi: 10.1021/om800549q
7. [7]
  J.B. Peng, F.P. Wu, X.F. Wu, Chem. Rev. 119 (2018) 2090–2127. doi: 10.1021/acs.chemrev.8b00068
8. [8]
  R. Jana, T.P. Pathak, M.S. Sigman, Chem. Rev. 111 (2011) 1417–1492. doi: 10.1021/cr100327p
9. [9]
  A.C. Bissember, A. Levina, G.C. Fu, J. Am. Chem. Soc. 134 (2012) 14232–14237. doi: 10.1021/ja306323x
10. [10]
  M.R. Kwiatkowski, E.J. Alexanian, Acc. Chem. Res. 52 (2019) 1134–1144. doi: 10.1021/acs.accounts.9b00044
11. [11]
  R. Kranthikumar, Organometallics. 41 (2022) 667–679. doi: 10.1021/acs.organomet.2c00032
12. [12]
  K. Nagahara, I. Ryu, M. Komatsu, N. Sonoda, J. Am. Chem. Soc. 119 (1997) 5465–5466. doi: 10.1021/ja964124g
13. [13]
  M. Sardana, J. Bergman, C. Ericsson, et al., J. Org. Chem. 84 (2019) 16076–16085. doi: 10.1021/acs.joc.9b02575
14. [14]
  G.M. Torres, Y. Liu, B.A. Arndtsen, Science (1979) 368 (2020) 318–323. doi: 10.1126/science.aba5901
15. [15]
  S.J. Ton, K.T. Neumann, P. Nørby, T. Skrydstrup, J. Am. Chem. Soc. 143 (2021) 17816–17824. doi: 10.1021/jacs.1c09170
16. [16]
  Y.H. Zhao, X.W. Gu, X.F. Wu, Org. Chem. Front. 11 (2024) 442–447. doi: 10.1039/d3qo01688a
17. [17]
  D.J.P. Kornfilt, D.W.C. MacMillan, J. Am. Chem. Soc. 141 (2019) 6853–6858. doi: 10.1021/jacs.9b03024
18. [18]
  X. Zhao, D.W.C. MacMillan, J. Am. Chem. Soc. 142 (2020) 19480–19486. doi: 10.1021/jacs.0c09977
19. [19]
  T. Constantin, M. Zanini, A. Regni, et al., Science (1979) 367 (2020) 1021–1026. doi: 10.1126/science.aba2419
20. [20]
  B. Górski, A.L. Barthelemy, J.J. Douglas, F. Juliá, D. Leonori, Nat. Catal. 4 (2021) 623–630. doi: 10.1038/s41929-021-00652-8
21. [21]
  A. Cai, W. Yan, C. Wang, W. Liu, Angew. Chem. Int. Ed. 60 (2021) 27070–27077. doi: 10.1002/anie.202111993
22. [22]
  A. Dewanji, L. van Dalsen, J.A. Rossi-Ashton, et al., Nat. Chem. 15 (2022) 43–52. doi: 10.1038/s41557-022-01092-y
23. [23]
  B. Lu, Z. Zhang, M. Jiang, et al., Angew. Chem. Int. Ed. 62 (2023) e202309460. doi: 10.1002/anie.202309460
24. [24]
  G.E.M. Crisenza, D. Mazzarella, P. Melchiorre, J. Am. Chem. Soc. 142 (2020) 5461–5476. doi: 10.1021/jacs.0c01416
25. [25]
  P. Huang, C. Lv, H. Song, et al., Green. Chem. 26 (2024) 7198–7205. doi: 10.1039/d4gc00728j
26. [26]
  T. Patra, S. Mukherjee, J. Ma, F. Strieth-Kalthoff, F. Glorius, Angew. Chem. Int. Ed. 58 (2019) 10514–10520. doi: 10.1002/anie.201904671
27. [27]
  X.K. Qi, M.J. Zheng, C. Yang, et al., J. Am. Chem. Soc. 145 (2023) 16630–16641. doi: 10.1021/jacs.3c04073
28. [28]
  B. Shi, M. Xiao, J.P. Zhao, et al., J. Am. Chem. Soc. 146 (2024) 26622–26629. doi: 10.1021/jacs.4c10328
29. [29]
  Y. Jia, K. Zhang, L.Q. Lu, Y. Cheng, W.J. Xiao, ACS. Catal. 14 (2024) 13550–13556. doi: 10.1021/acscatal.4c04249
30. [30]
  P.Z. Wang, Z. Zhang, M. Jiang, J.R. Chen, W.J. Xiao, Angew. Chem. Int. Ed. 63 (2024) e202411469.
31. [31]
  X.K. He, L.Q. Lu, B.R. Yuan, et al., J. Am. Chem. Soc. 146 (2024) 18892–18898. doi: 10.1021/jacs.4c07096
32. [32]
  B. Lu, F.S. Bao, Z.W. He, W.J. Xiao, J.R. Chen, Chin. J. Chem. 42 (2024) 990–996. doi: 10.1002/cjoc.202300733
33. [33]
  Y.L. Tu, B.B. Zhang, B.S. Qiu, Z.X. Wang, X.Y. Chen, Angew. Chem. Int. Ed. 62 (2023) e202310764. doi: 10.1002/anie.202310764
1. [1]
  Zhi-Peng Bao , Hefei Yang , Ru-Han A , Yuanrui Wang , Xiao-Feng Wu . Carbonylative five-component synthesis of amides and esters with α-quaternary carbon center. Chinese Chemical Letters, 2025, 36(11): 111150-. doi: 10.1016/j.cclet.2025.111150
2. [2]
  Jingyan Liu , Wanting Liang , Changfeng Wan , Jie-Ping Wan . Photocatalytic free radical geminal carboamination of α-diazo esters toward chromone-derived α-amino acids. Chinese Chemical Letters, 2026, 37(5): 112202-. doi: 10.1016/j.cclet.2025.112202
3. [3]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
4. [4]
  Lei Shen , Yang Zhang , Linlin Zhang , Chuanwang Liu , Zhixian Ma , Kangjiang Liang , Chengfeng Xia . Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes. Chinese Chemical Letters, 2024, 35(4): 108742-. doi: 10.1016/j.cclet.2023.108742
5. [5]
  Lei Li , Guang Yang , Tianbai Xiong , Tingzhu Duan , Jia Wang , Xin Wang . Metal-free click polymerization of thiols and chalcone-derived internal olefins in air to prepare functional clusteroluminescent polythioethers for dual-response fluorescent probe. Chinese Chemical Letters, 2025, 36(11): 111374-. doi: 10.1016/j.cclet.2025.111374
6. [6]
  Xiu-Mei Xie , Hongyang Zhang , Shao-Xuan Gong , Hong-Xia Sun , Yu-Ting Liu , Xue-Ling Chen , Shuming Chen , Tian-Yu Gao , Wai-Yeung Wong , Zhen Zhang , Da-Gang Yu . Carbonylation of C(sp³)–H bonds with CO₂: Facile synthesis of 2,4-quinolinediones and related luminescent materials. Chinese Chemical Letters, 2026, 37(3): 112003-. doi: 10.1016/j.cclet.2025.112003
7. [7]
  Zhengzhong Zhu , Shaojun Hu , Zhi Liu , Lipeng Zhou , Chongbin Tian , Qingfu Sun . A cationic radical lanthanide organic tetrahedron with remarkable coordination enhanced radical stability. Chinese Chemical Letters, 2025, 36(2): 109641-. doi: 10.1016/j.cclet.2024.109641
8. [8]
  Xiao-Bo Liu , Ren-Ming Liu , Xiao-Di Bao , Hua-Jian Xu , Qi Zhang , Yu-Feng Liang . Nickel-catalyzed reductive formylation of aryl halides via formyl radical. Chinese Chemical Letters, 2024, 35(12): 109783-. doi: 10.1016/j.cclet.2024.109783
9. [9]
  Hong-Qiang Dong , Shang-Bo Yu , Shu-Meng Wang , Jia-Hao Zhao , Xu-Guan Bai , Shi-Xing Lei , Zhen-Nan Tian , Jia Tian , Kang-Da Zhang , Lu Wang , Zhan-Ting Li , Shigui Chen . Construction of radical halogen-bonded organic frameworks with enhanced magnetism and conductivity. Chinese Chemical Letters, 2025, 36(8): 110730-. doi: 10.1016/j.cclet.2024.110730
10. [10]
  Wenjuan Liu , Shanshan Zhang , Yu Wang , Bin Fang , Weirui Wang , Shujing Song , Tomohiro Hakozaki . Three-channel imaging reveals the comprehensive protein modifications and their impact on skin appearance induced by multiple stimuli. Chinese Chemical Letters, 2025, 36(6): 111182-. doi: 10.1016/j.cclet.2025.111182
11. [11]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
12. [12]
  Le Zhang , Hui-Yu Xie , Xin Li , Li-Ying Sun , Ying-Feng Han . SOMO-HOMO level conversion in triarylmethyl-cored N-heterocyclic carbene-Au(I) complexes triggered by selecting coordination halogens. Chinese Chemical Letters, 2024, 35(11): 109465-. doi: 10.1016/j.cclet.2023.109465
13. [13]
  Huaixiang Yang , Miao-Miao Li , Aijun Zhang , Jiefei Guo , Yongqi Yu , Wei Ding . Visible-light-induced photocatalyst- and metal-free radical phosphinoyloximation of alkenes with tert-butyl nitrite as bifunctional reagent. Chinese Chemical Letters, 2025, 36(3): 110425-. doi: 10.1016/j.cclet.2024.110425
14. [14]
  Denghong Zhao , Mingwei Yang , Yichuan Zhang , Long Qin , Hang Liu , Hongji Chen , Maoguo Tan , Zhongyi Yin , Bin Sun , Yu Shen , Haijiao Xie , Heyan Jiang . Microwave assisted metal-free catalysts preparation from waste plastics for efficient pollutants degradation: Interesting relationship between plastic types and nonradical/radical pathways. Chinese Chemical Letters, 2026, 37(3): 111631-. doi: 10.1016/j.cclet.2025.111631
15. [15]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
16. [16]
  Jie Li , Huida Qian , Deyang Pan , Wenjing Wang , Daliang Zhu , Zhongxue Fang . Efficient Synthesis of Anethaldehyde Induced by Visible Light. University Chemistry, 2024, 39(4): 343-350. doi: 10.3866/PKU.DXHX202310076
17. [17]
  Qi Zhang , Ziyu Liu , Hongxia Tan , Jun Tong , Dazhen Xu . Research Progress on Direct Synthesis of β-Hydroxy Sulfones via Difunctionalization of Olefins. University Chemistry, 2025, 40(11): 199-209. doi: 10.12461/PKU.DXHX202412064
18. [18]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879
19. [19]
  Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018
20. [20]
  Chunxiu Yu , Zelin Wu , Hongle Shi , Lingyun Gu , Kexin Chen , Chuan-Shu He , Yang Liu , Heng Zhang , Peng Zhou , Zhaokun Xiong , Bo Lai . Insights into the electron transfer mechanisms of peroxydisulfate activation by modified metal-free acetylene black for degradation of sulfisoxazole. Chinese Chemical Letters, 2024, 35(8): 109334-. doi: 10.1016/j.cclet.2023.109334

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1937)
HTML views(39)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142