Citation: Hong-Tao Zhang, Li-Jun Gu, Xiang-Zhong Huang, Rui Wang, Cheng Jin, Gan-Peng Li. Synthesis of indol-3-yl aryl ketones through visible-light-mediated carbonylation[J]. Chinese Chemical Letters, ;2016, 27(02): 256-260. doi: 10.1016/j.cclet.2015.10.012 shu

Synthesis of indol-3-yl aryl ketones through visible-light-mediated carbonylation

a.
a. Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming 650500, China;
b.
b. Engineering Research Center of Biopolymer Functional Materials of Yunnan, Yunnan Minzu University, Kunming 650500, China;
c.
c. New United Group Company Limited, Changzhou 213166, China

Corresponding author: Li-Jun Gu, Gan-Peng Li,
Received Date: 20 July 2015
Available Online: 18 September 2015
Fund Project: We are grateful for the financial support from the Educational Bureau of Yunnan Province (No. 2010Y431) (No. 2010Y431)the State Ethnic Affairs Commission ([8_TD$DIF]No. 12YNZ05). ([8_TD$DIF]No. 12YNZ05)

A visible-light-catalyzed synthesis of indol-3-yl aryl ketones from aryldiazonium salts, CO and indoles at room temperature was developed. This process provides a useful method for the preparation of diverse indol-3-yl aryl ketones from readily accessible reactants under base-free, acid-free and transition-metalfree conditions.
- Indol-3-yl aryl ketones,
- Carbonylation,
- Visible-light,
- Aryldiazonium salts,
- Indoles
1. [1]
  [1] (a) G.L. Regina, T. Sarkar, R. Bai, et al., New arylthioindoles and related bioisosteres at the sulfur bridging group. 4. Synthesis, tubulin polymerization, cell growth inhibition, and molecular modeling studies, J. Med. Chem. 52 (2009) 7512-7527;
2. [2]
  (b) I. Nicolaou, V.J. Demopoulos, Substituted pyrrol-1-ylacetic acids that combine aldose reductase enzyme inhibitory activity and ability to prevent the nonenzymatic irreversiblemodification of proteins frommonosaccharides, J.Med. Chem. 46 (2003) 417-426;
3. [3]
  (c) P.M. Fresneda, P. Molina, M.A. Saez, The first synthesis of the bis(indole) marine alkaloid caulersin, Synlett 1999 (1999) 1651-1653;
4. [4]
  (d) L.J. Zhang, X. Xue, C.H. Xu, et al., Rhodium-catalyzed decarbonylative direct C2-arylation of indoles with aryl carboxylic acids, ChemCatChem6 (2014) 3069-3074;
5. [5]
  (e) S. Kathiravan, I.A. Nicholls, Rhodium(Ⅲ)-catalysed aerobic synthesis of highly functionalized indoles from N-arylurea under mild conditions through C-H activation, Chem. Commun. 50 (2014) 14964-14967;
6. [6]
  (f) M. Kim, N.K.Mishra, J. Park, et al., Decarboxylative acylation of indolineswithaketo acids under palladium catalysis: a facile strategy for the synthesis of 7-substituted indoles, Chem. Commun. 50 (2014) 14249-14252; For a few selected references, see:
7. [7]
  [2] (a) J.E. Saxton, Recent progress in the chemistry of the monoterpenoid indole alkaloids, Nat. Prod. Rep. 14 (1997) 559-590;
8. [8]
  (b) M. Toyota, M. Ihara, Recent progress in the chemistry of non-monoterpenoid indole alkaloids, Nat. Prod. Rep. 15 (1998) 327-340;
9. [9]
  (c) M. Bandini, A. Eichholzer, Catalytic functionalization of indoles in a new dimension, Angew. Chem. Int. Ed. 48 (2009) 9608-9644;
10. [10]
  (d) Q.Q. Yang, C. Xiao, L.Q. Lu, et al., Synthesis of indoles through highly efficient cascade reactions of sulfur ylides and N-(ortho-chloromethyl)aryl amides, Angew. Chem. Int. Ed. 51 (2012) 9137-9140;
11. [11]
  (e) X. Zhang, Y.F. Li, H. Shi, et al., Rhodium(Ⅲ)-catalyzed intramolecular amidoarylationand hydroarylation of alkyne viaC-Hactivation:switchablesynthesis of 3,4-fused tricyclic indoles and chromans, Chem. Commun. 50 (2014) 7306-7309;
12. [12]
  (f) M. Inman, C.J. Moody, Indole synthesis-something old, something new, Chem. Sci. 4 (2013) 29-41;
13. [13]
  (g) G.R.Humphrey, J.T. Kuethe, Practical methodologies for the synthesis of indoles, Chem. Rev. 106 (2006) 2875-2911;
14. [14]
  (h) L.J. Gu, C. Jin, H.T.Zhang, L.Z. Zhang,Copper-catalyzedaerobicoxidativecleavage ofC-Cbonds inepoxides leading to aryl ketones, J.Org.Chem.79(2014)8453-8456;
15. [15]
  (i) R. Leurs, P.L.Chazot, F.C. Shenton, H.D. Lim, I.J.D. Esch,Molecular andbiochemical pharmacology of the histamine H₄ receptor, Br. J. Pharmacol. 157 (2009) 14-23;
16. [16]
  (j) P. Sang, Z.K. Chen, J.W. Zou, Y.H. Zhang, K₂CO₃ promoted direct sulfenylation of indoles: a facile approach towards 3-sulfenylindoles, Green Chem. 15 (2013) 2096-2100; For selected examples, see:
17. [17]
  [3] (a) M.M. Faul, L.L. Winnerosk, Palladium-catalyzed acylation of a 1,2-disubstituted 3-indolylzinc chloride, Tetrahedron Lett. 38 (1997) 4749-4752;
18. [18]
  (b) S.K. Guchhait, M. Kashyap, H. Kamble, ZrCl4-mediated regio-and chemoselective Friedel-Crafts acylation of indole, J. Org. Chem. 76 (2011) 4753-4758;
19. [19]
  (c) H. Johansson, A. Urruticoechea, I. Larsen, D.S. Pedersen, A scalable method for regioselective 3-acylation of 2-substituted indoles under basic conditions, J. Org. Chem. 80 (2015) 471-478;
20. [20]
  (d) N.N. Wan, Y.H. Hui, Z.F. Xie, J.D. Wang, Friedel-crafts alkylation of indoles with nitroalkenes catalyzed by Zn(Ⅱ)-thiourea complex, Chin. J. Chem. 30 (2012) 311-315;
21. [21]
  (e) P. Zhang, T.B. Xiao, S.W. Xiong, X.C. Dong, L. Zhou, Synthesis of 3-acylindoles by visible-light induced intramolecular oxidative cyclization of o-alkynylated N,N-dialkylamines, Org. Lett. 14 (2014) 3264-3267;
22. [22]
  (f) L. Yu, P.H. Li, L. Wang, Copper-promoted decarboxylative direct C3-acylation of N-substituted indoles with α-oxocarboxylic acids, Chem. Commun. 49 (2013) 2368-2370; For selected examples, see:
23. [23]
  [4] (a) J.H. Wynne, C.T. Lloyd, S.D. Jensen, S. Boson, W.M. Stalick, 3-Acylindoles via a one-pot, regioselective Friedel-Crafts reaction, Synthesis 14 (2004) 2277-2282;
24. [24]
  (b) K. Yeung, M.E. Farkas, Z.L. Qiu, Z. Yang, Friedel-crafts acylation of indoles in acidic imidazolium chloroaluminate ionic liquid at room temperature, Tetrahedron Lett. 43 (2002) 5793-5795;
25. [25]
  (c) T. Okauchi, M. Itonaga, T. Minami, et al., General method for acylation of indoles at the 3-position with acyl chlorides in the presence of dialkylaluminum chloride, Org. Lett. 2 (2000) 1485-1487; For selected examples, see:
26. [26]
  [5] W. Anthony, Novel synthesis of heterocyclic ketones, J. Org. Chem. 25 (1960) 2049-2053.
27. [27]
  [6] J. Bergman, L. Venemalm, Intramolecular, ring closure of α,β-unsaturated 3-acylindoles, Tetrahedron Lett. 28 (1987) 3741-3744.
28. [28]
  [7] (a) Y.H. Ma, J.S. You, F.J. Song, Facile access to 3-acylindoles through palladiumcatalyzed addition of indoles to nitriles: the one-pot synthesis of indenoindolones, Chem. Eur. J. 19 (2013) 1189-1193;
29. [29]
  (b) M.N. Zhao, L.F. Ran, M. Chen, et al., Palladium-catalyzed carbonylation of indoles for synthesis of indol-3-yl aryl ketones, ACS Catal. 5 (2015) 1210-1213;
30. [30]
  (c) W.L. Wu, W.P. Su, Mild and selective Ru-catalyzed formylation and Fe-catalyzed acylation of free (N-H) indoles using anilines as the carbonyl source, J. Am. Chem. Soc. 133 (2011) 11924-11927;
31. [31]
  (d) L.J. Gu, J.Y. Liu, L.Z. Zhang, Y. Xiong, R. Wang, Synthesis of 3-acylindoles via decarboxylative cross-coupling reaction of free (N-H) indoles with α-oxocarboxylic acids, Chin. Chem. Lett. 25 (2014) 90-92; For selected examples, see:
32. [32]
  [8] (a) J. Xuan, W.J. Xiao, Visible-light photoredox catalysis, Angew. Chem. Int. Ed. 51 (2012) 6828-6838;
33. [33]
  (b) T.P. Yoon, M.A. Ischay, J. Du, Visible light photocatalysis as a greener approach to photochemical synthesis, Nat. Chem. 2 (2010) 527-532;
34. [34]
  (c) C.K. Prier, D.A. Rankic, D.W.C. MacMillan, Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis, Chem. Rev. 113 (2013) 5322-5363;
35. [35]
  (d) K. Zeitler, Photoredox catalysis with visible light, Angew. Chem. Int. Ed. 48 (2009) 9785-9789;
36. [36]
  (e) L. Shi, W. Xia, Photoredox functionalization of C-H bonds adjacent to a nitrogen atom, Chem. Soc. Rev. 41 (2012) 7687-7697;
37. [37]
  (f) J.W. Tucker, C.R.J. Stephenson, Shining light on photoredox catalysis: theory and synthetic applications, J. Org. Chem. 77 (2012) 1617-1622;
38. [38]
  (g) D.M. Schultz, T.P. Yoon, Solar synthesis: prospects in visible light photocatalysis, Science 343 (2014) 1239176;
39. [39]
  (h) M. Majek, F. Filace, A.J. Wangelin, On the mechanism of photocatalytic reactions with eosin Y, Beilstein J. Org. Chem. 10 (2014) 981-989; For selected reviews on visible-light photoredox catalysis, see:
40. [40]
  [9] D.A. Nicewicz, D.W.C. MacMillan, Merging photoredox catalysis with organocatalysis: the direct asymmetric alkylation of aldehydes, Science 322 (2008) 77-80.
41. [41]
  [10] (a) H.J. Jiang, Y.Z. Cheng, R.Z. Wang, Y. Zhang, S.Y. Yu, Synthesis of isoquinolines via visible light-promoted insertion of vinyl isocyanides with diaryliodonium salts, Chem. Commun. 50 (2014) 6164-6166;
42. [42]
  (b) Y. Xu, W. Zhang, Ag/AgBr-grafted graphite-like carbon nitride with enhanced plasmonic photocatalytic activity under visible light, ChemCatChem 5 (2013) 2343-2351;
43. [43]
  (c) G.B. Deng, Z.Q. Wang, J.D. Xia, et al., Tandem cyclizations of 1,6-enynes with arylsulfonyl chlorides by using visible-light photoredox catalysis, Angew. Chem. Int. Ed. 52 (2013) 1535-1538;
44. [44]
  (d) J.D. Xia, G.B. Deng, M.B. Zhou, et al., Reusable visible light photoredox catalysts: catalyzed benzylic C(sp3)-H functionalization/carbocyclization reactions, Synlett 18 (2012) 2707-2713;
45. [45]
  (e) E.L. Tyson, Z.L. Niemeyer, T.P. Yoon, Redox mediators in visible light photocatalysis: photocatalytic radical thiol-ene additions, J. Org. Chem. 79 (2014) 1427-1436;
46. [46]
  (f) L.J. Gu, C. Jin, J.Y. Liu, H.Y. Ding, B.M. Fan, Transition-metal-free, visible-light induced cyclization of arylsulfonyl chlorides with 2-isocyanobiphenyls to produce phenanthridines, Chem. Commun. 50 (2014) 4643-4645;
47. [47]
  (g) J. Xuan, X. Xia, T. Zeng, et al., Visible-light-induced formal [3 + 2] cycloaddition for pyrrole synthesis under metal-free conditions, Angew. Chem. Int. Ed. 53 (2014) 5653-5656;
48. [48]
  (h) J. Liu, Q. Liu, H. Yi, et al., Visible-light-mediated decarboxylation/oxidative amidation of a-keto acids with amines under mild reaction conditions using O2, Angew. Chem. Int. Ed. 53 (2014) 502-506;
49. [49]
  (i) D.P. Hari, B. König, Synthetic applications of eosin Y in photoredox catalysis, Chem. Commun. 50 (2014) 6688-6699;
50. [50]
  (j) A.K.Yadav, V.P. Srivastava, L.D.S.Yadav, Visible-light-mediatedeosinYcatalyzed aerobic desulfurization of thioamides into amides, New J. Chem. 37 (2013) 4119-4124;
51. [51]
  (k) T.B. Xiao, L.Y. Li, G.L. Lin, et al., Synthesis of 6-substituted phenanthridines by metal-free, visible-light induced aerobic oxidative cyclization of 2-isocyanobiphenyls with hydrazines, Green Chem. 16 (2014) 2418-2421;
52. [52]
  (l) M.N.Hopkinson, B. Sahoo, J. Li, F. Glorius,Dual catalysis sees the light: combining photoredox with organo-, acid, and transition-metal catalysis, Chem. Eur. J. 20 (2014) 3874-3886;
53. [53]
  (m) C. Yu, N. Iqbal, S. Park, E.J. Cho, Selective difluoroalkylation of alkenes by using visible light photoredox catalysis, Chem. Commun. 50 (2014) 12884-12887;
54. [54]
  (n) J.C. Tellis, D.N. Primer, G.A. Molander, Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis, Science 345 (2014) 433-436;
55. [55]
  (o) Z. Zuo, D.T. Ahneman, L. Chu, et al., Merging photoredox with nickel catalysis: coupling of a-carboxyl sp3-carbonswith aryl halides, Science 345 (2014) 437-440; For recent selected examples for visible-light photoredox catalysts, see:
56. [56]
  [11] (a) D.P. Hari, P. Schroll, B. König, Metal-free, visible-light-mediated direct C-H arylation of heteroarenes with aryl diazonium salts, J. Am. Chem. Soc. 134 (2012) 2958-2961;
57. [57]
  (b) M. Majek, A.J. Wangelin, Metal-free carbonylations by photoredox catalysis, Angew. Chem. Int. Ed. 54 (2015) 2270-2274;
58. [58]
  (c) W. Guo, L.Q. Lu, Y. Wang, et al., Metal-free, room-temperature, radical alkoxycarbonylation of aryldiazonium salts through visible-light photoredox catalysis,, Angew. Chem. Int. Ed. 54 (2015) 2265-2269;
59. [59]
  (d) T. Hering, D.P. Hari, B. König, Visible-light-mediated a-arylation of enol acetates using aryl diazonium salts, J. Org. Chem. 77 (2012) 10347-10352;
60. [60]
  (e) F.P. Crisóstomo, T. Martin, R. Carrillo, ascorbic acid as an initiator for the direct C-H arylation of (hetero)arenes with anilines nitrosated in situ, Angew. Chem. Int. Ed. 53 (2014) 2181-2185;
61. [61]
  (f) L.J. Gu, C. Jin, J.Y. Yan, Metal-free, visible-light-mediated transformation of aryl diazonium salts and (hetero)arenes: an efficient route to aryl ketones, Green Chem. 17 (2015) 3733-3736.
62. [62]
  [12] T. Kawamoto, T. Okada, D.P. Curran, I. Ryu, Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane, Org. Lett. 15 (2013) 2144-2147.
63. [63]
  [13] B. Sahoo, M.N. Hopkinson, F. Glorius, Combining gold and photoredox catalysis: visible light-mediated oxy-and aminoarylation of alkenes, J. Am. Chem. Soc. 135 (2013) 5505-5508.
64. [64]
  [14] D.P. Hari, B. König, The photocatalyzed Meerwein arylation: classic reaction of aryl diazonium salts in a new light, Angew. Chem. Int. Ed. 52 (2013) 4734-4743.
1. [1]
  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
2. [2]
  Chunyan Yang , Qiuyu Rong , Fengyin Shi , Menghan Cao , Guie Li , Yanjun Xin , Wen Zhang , Guangshan Zhang . Rationally designed S-scheme heterojunction of BiOCl/g-C₃N₄ for photodegradation of sulfamerazine: Mechanism insights, degradation pathways and DFT calculation. Chinese Chemical Letters, 2024, 35(12): 109767-. doi: 10.1016/j.cclet.2024.109767
3. [3]
  Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
4. [4]
  Tian-Yu Gao , Xiao-Yan Mo , Shu-Rong Zhang , Yuan-Xu Jiang , Shu-Ping Luo , Jian-Heng Ye , Da-Gang Yu . Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO₂. Chinese Chemical Letters, 2024, 35(7): 109364-. doi: 10.1016/j.cclet.2023.109364
5. [5]
  Ping Lu , Baoyin Du , Ke Liu , Ze Luo , Abiduweili Sikandaier , Lipeng Diao , Jin Sun , Luhua Jiang , Yukun Zhu . Heterostructured In2O3/In2S3 hollow fibers enable efficient visible-light driven photocatalytic hydrogen production and 5-hydroxymethylfurfural oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100361-100361. doi: 10.1016/j.cjsc.2024.100361
6. [6]
  Feiyang Liu , Liuhong Song , Miaoyu Fu , Zhi Zheng , Gang Xie , Junlong Zhao . Tryptophan’s Employment Journey. University Chemistry, 2024, 39(9): 16-21. doi: 10.12461/PKU.DXHX202404037
7. [7]
  Jing Wang , Zenghui Li , Xiaoyang Liu , Bochao Su , Honghong Gong , Chao Feng , Guoping Li , Gang He , Bin Rao . Fine-tuning redox ability of arylene-bridged bis(benzimidazolium) for electrochromism and visible-light photocatalysis. Chinese Chemical Letters, 2024, 35(9): 109473-. doi: 10.1016/j.cclet.2023.109473
8. [8]
  Guanyang Zeng , Xingqiang Liu , Liangqiao Wu , Zijie Meng , Debin Zeng , Changlin Yu . Novel visible-light-driven I- doped Bi2O2CO3 nano-sheets fabricated via an ion exchange route for dye and phenol removal. Chinese Journal of Structural Chemistry, 2024, 43(12): 100462-100462. doi: 10.1016/j.cjsc.2024.100462
9. [9]
  Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
10. [10]
  Xiao Xiao , Biao Chen , Jia-Wei Li , Jun-Bo Zheng , Xu Wang , Hang Zhao , Fen-Er Chen . Nitrite-catalyzed economic and sustainable bromocyclization of tryptamines/tryptophols to access hexahydropyrrolo[2,3-b]indoles/tetrahydrofuroindolines in batch and flow. Chinese Chemical Letters, 2024, 35(7): 109280-. doi: 10.1016/j.cclet.2023.109280
11. [11]
  Hui Peng , Xiao Wang , Weiguo Huang , Shuiyue Yu , Linghang Kong , Qilin Wei , Jialong Zhao , Bingsuo Zou . Efficient tunable visible and near-infrared emission in Sb³⁺/Sm³⁺-codoped Cs₂NaLuCl₆ for near-infrared light-emitting diode, triple-mode fluorescence anti-counterfeiting and information encryption. Chinese Chemical Letters, 2024, 35(11): 109462-. doi: 10.1016/j.cclet.2023.109462
12. [12]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
13. [13]
  Xuhui Fan , Fan Wang , Mengjiao Li , Faiza Meharban , Yaying Li , Yuanyuan Cui , Xiaopeng Li , Jingsan Xu , Qi Xiao , Wei Luo . Visible light excitation on CuPd/TiN with enhanced chemisorption for catalyzing Heck reaction. Chinese Chemical Letters, 2025, 36(1): 110299-. doi: 10.1016/j.cclet.2024.110299
14. [14]
  Tingting Liu , Pengfei Sun , Wei Zhao , Yingshuang Li , Lujun Cheng , Jiahai Fan , Xiaohui Bi , Xiaoping Dong . Magnesium doping to improve the light to heat conversion of OMS-2 for formaldehyde oxidation under visible light irradiation. Chinese Chemical Letters, 2024, 35(4): 108813-. doi: 10.1016/j.cclet.2023.108813
15. [15]
  Ziruo Zhou , Wenyu Guo , Tingyu Yang , Dandan Zheng , Yuanxing Fang , Xiahui Lin , Yidong Hou , Guigang Zhang , Sibo Wang . Defect and nanostructure engineering of polymeric carbon nitride for visible-light-driven CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(3): 100245-100245. doi: 10.1016/j.cjsc.2024.100245
16. [16]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
17. [17]
  Xin Wang , Changzhao Chen , Qishen Wang , Kai Dai . Graphene quantum dot modified Bi2MoO6 nanoflower for efficient degradation of BPA under visible light. Chinese Journal of Structural Chemistry, 2024, 43(12): 100473-100473. doi: 10.1016/j.cjsc.2024.100473
18. [18]
  Yi Liu , Zhe-Hao Wang , Guan-Hua Xue , Lin Chen , Li-Hua Yuan , Yi-Wen Li , Da-Gang Yu , Jian-Heng Ye . Photocatalytic dicarboxylation of strained C–C bonds with CO₂ via consecutive visible-light-induced electron transfer. Chinese Chemical Letters, 2024, 35(6): 109138-. doi: 10.1016/j.cclet.2023.109138
19. [19]
  Yiyue Ding , Qiuxiang Zhang , Lei Zhang , Qilu Yao , Gang Feng , Zhang-Hui Lu . Exceptional activity of amino-modified rGO-immobilized PdAu nanoclusters for visible light-promoted dehydrogenation of formic acid. Chinese Chemical Letters, 2024, 35(7): 109593-. doi: 10.1016/j.cclet.2024.109593
20. [20]
  Qiongqiong Wan , Yanan Xiao , Guifang Feng , Xin Dong , Wenjing Nie , Ming Gao , Qingtao Meng , Suming Chen . Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids. Chinese Chemical Letters, 2024, 35(4): 108775-. doi: 10.1016/j.cclet.2023.108775

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(695)
HTML views(17)

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