Citation: CHAN Chung-Sum, CHAN Kin-Shing*. Aldehydic Carbon-Hydrogen Bond Activation with Iridium(Ⅲ) Porphyrin β-Hydroxyethyl[J]. Chinese Journal of Inorganic Chemistry, ;2014, 30(1): 75-84. doi: 10.11862/CJIC.2014.034 shu

Aldehydic Carbon-Hydrogen Bond Activation with Iridium(Ⅲ) Porphyrin β-Hydroxyethyl

1.
Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China

Received Date: 10 July 2013
Available Online: 6 November 2013
Fund Project:

Iridium(Ⅲ) porphyrin β-hydroxyethyl, Ir^Ⅲ(ttp)CH₂CH₂OH (ttp=5,10,15,20-tetratolylporphyrinato dianion), was found to selectively cleave the aldehydic carbon-hydrogen bonds of aryl aldehydes giving iridium acyl complexes. Iridium acyl complexes are good candidates for the studies on carbonylation and decarbonylation reactions as well as potential functionalization. The carbon-hydrogen bond activation (CHA) is proposed to occur through the initial β-hydroxyl elimination of Ir^Ⅲ(ttp)CH₂CH₂OH to give Ir^Ⅲ(ttp)OH, which then undergoes σ-bond metathesis with the aldehydic C-H bond.
- coordination, iridium, carbonylation and decarbonylation reaction,
1. [1]
  [1] (a) Arndtsen B A, Bergman R G. Science, 1995, 270:1970-1973
2. [2]
  (b) Goldberg K I, Goldman A S., Eds. Activation and Func-tionalization of C-H Bonds; ACS Symposium Series 885; Washington, DC: American Chemical Society, 2004.
3. [3]
  (c) Jun C-H, Lee J H. Pure Appl. Chem. 2004, 76:577-587
4. [4]
  (d) Jones W D. Inorg. Chem., 2005, 44:4475-4484
5. [5]
  [2] (a) Jones W D, Feher F J. Organometallics, 1983, 2:562-563
6. [6]
  (b) Periana R A, Bergman R G. Organometallics, 1984, 3: 508-510
7. [7]
  (c) Jones W D. Feher F J. Acc. Chem. Res., 1989, 22:91-100
8. [8]
  [3] (a) Suggs J W. J. Am. Chem. Soc., 1978, 100:640-641
9. [9]
  (b) Milstein D. Organometallics, 1982, 1:1549-1551
10. [10]
  (c) Gutiérrez-Puebla E, Monge A, Paneque M, et al. J. Am. Chem. Soc., 1999, 121:248-249.
11. [11]
  [4] (a) Eschinazi H E, Pines H. J. Org. Chem., 1959, 24:1369-1369
12. [12]
  (b) Eschinazi H E. J. Am. Chem. Soc., 1959, 81:2905-2906
13. [13]
  (c) Tsuji J, Ohno K. J. Am. Chem. Soc., 1968, 90:94-98
14. [14]
  (d) Domazetis G, Tarpey B, Dolphin D, et al. Chem. Commun., 1980, 939-940
15. [15]
  (e) Tsuji J, Ohno K. J. Am. Chem. Soc., 1968, 90:99-107
16. [16]
  (f) Doughty D H, Pignolet L H. J. Am. Chem. Soc., 1978, 100:7083-7085
17. [17]
  (g) Beck C M, Rathmill S E, Park Y J, et al. Organometallics, 1999, 18:5311-5317
18. [18]
  [5] Choi K S, Chiu P F, Chan K S. Organometallics, 2010, 29: 624-629
19. [19]
  [6] Fung H S. Ph.D Thesis. of the Chinese University of Hong Kong. 2012.
20. [20]
  [7] Chan K S, Lau C M, Yeung S K, et al. Organometallics, 2007, 26:1981-1985
21. [21]
  [8] Chan K S, Lau C M. Organometallics, 2006, 25:260-265
22. [22]
  [9] Song X, Chan K S. Organometallics, 2007, 26:965-970
23. [23]
  [10] Lee S Y, Lai T H, Chan K S, et al. Organometallics, 2011, 30:3691-3693
24. [24]
  [11] (a) Fung H S, Li B Z, Chan K S. Organometallics, 2010, 29: 4421-4423
25. [25]
  (b) Fung H S, Li B Z, Chan K S. Organometallics, 2012, 31: 570-579
26. [26]
  [12] (a) Li B Z, Song X, Chan K S, et al. Organometallics, 2010, 29:2001-2003
27. [27]
  (b) Li B Z, Fung, H S, Chan, K S, et al. Organometallics, 2011, 30, 1984-1990
28. [28]
  [13] Cheung C W, Chan K S. Organometallics, 2011, 30:4269-4283
29. [29]
  [14] Tsang J Y K, Chan K S. Can. J. Chem., 2011, 89:1506-1511
30. [30]
  [15] Luo Y R. Comprehensive Handbook of Chemical Bond Energies, CRC Press, Boca Raton, FL, 2007.
31. [31]
  [16] (a) Ogoshi H, Setsune J I, Yoshida Z I. J. Organomet. Chem., 1978, 159:317-328
32. [32]
  (b) Yeung S K, Chan K S. Organometallics, 2005, 24:6426-6430
33. [33]
  (c) van der Ent A, Onderdelinden A L. Inorg. Synth., 1973, 14:92-95
1. [1]
  Xuyu WANG , Xinran XIE , Dengke CAO . Photoreaction characteristics and luminescence modulation in phosphine-anthracene-based Au(Ⅰ) and Ir(Ⅲ) complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1513-1522. doi: 10.11862/CJIC.20250113
2. [2]
  Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073
3. [3]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
4. [4]
  Zuozhong Liang , Lingling Wei , Yiwen Cao , Yunhan Wei , Haimei Shi , Haoquan Zheng , Shengli Gao . Exploring the Development of Undergraduate Scientific Research Ability in Basic Course Instruction: A Case Study of Alkali and Alkaline Earth Metal Complexes in Inorganic Chemistry. University Chemistry, 2024, 39(7): 247-263. doi: 10.3866/PKU.DXHX202310103
5. [5]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
6. [6]
  Hanxue LIU , Shijie LI , Meng REN , Xuling XUE , Hongke LIU . Design and antitumor properties of dehydroabietic acid functionalized cyclometalated iridium(Ⅲ) complex. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1483-1494. doi: 10.11862/CJIC.20250031
7. [7]
  Qiaowen CHANG , Ke ZHANG , Guangying HUANG , Nuonan LI , Weiping LIU , Fuquan BAI , Caixian YAN , Yangyang FENG , Chuan ZUO . Syntheses, structures, and photo-physical properties of iridium phosphorescent complexes with phenylpyridine derivatives bearing different substituting groups. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 235-244. doi: 10.11862/CJIC.20240311
8. [8]
  Cunling Ye , Xitong Zhao , Hongfang Wang , Zhike Wang . A Formula for the Calculation of Complex Concentrations Arising from Side Reactions and Its Applications. University Chemistry, 2024, 39(4): 382-386. doi: 10.3866/PKU.DXHX202310043
9. [9]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
10. [10]
  Ruoxi RUN , Jikai ZHU , Lixia HAN , Zhiyin XIAO , Xiujuan JIANG , Jing JIN . Red light-induced CO-release from manganese carbonyl complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2575-2583. doi: 10.11862/CJIC.20250132
11. [11]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
12. [12]
  Dan PENG , Hao WANG , Yanyan WANG , Hongpeng YOU , Wuping LIAO . Synthesis and fluorescent properties of a one-dimensional Tb-calixarene complex as a luminescent thermometer material. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1859-1866. doi: 10.11862/CJIC.20250128
13. [13]
  Jiarong ZHU , Xiaohua ZHANG , Xinting XIONG , Xuliang NIE , Xiuying SONG , Miaomiao ZHANG , Dayong PENG , Xiuguang YI . Crystal structure, Hirshfeld surface analysis, and antifungal activity of five complexes based on 2,5-bis(carboxymethoxy)terephthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2358-2370. doi: 10.11862/CJIC.20250150
14. [14]
  Zhenghua ZHAO , Yufeng LIU , Qing ZHANG , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of zinc(Ⅱ), nickel(Ⅱ) and cadmium(Ⅱ) complexes constructed from a terphenyl-tricarboxylate ligand. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 170-180. doi: 10.11862/CJIC.20250161
15. [15]
  Zihao XU , Lirong GUO , Jinzhong GU . Syntheses, crystal structures, and catalytic properties of zinc(Ⅱ) and cadmium(Ⅱ) coordination polymers constructed from a dicarboxylate ligand. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 1063-1072. doi: 10.11862/CJIC.20250345
16. [16]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
17. [17]
  Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
18. [18]
  Sihan Wang , Chenxi Yu , Shuzhang Ran , Jiawei Chen , Shoutong Rao , Xinyi Liang , Ruiqi Dong , Guixiang Zeng , Guoqiang Wang , Jing Ma . 铁配合物合成与性质探究的数智化改进——大学化学实验中“磺基水杨酸合铁配合物的组成与稳定常数的测定”的创新设计. University Chemistry, 2026, 41(5): 36-49. doi: 10.12461/PKU.DXHX202511137
19. [19]
  Wenke ZHENG , Ce LIU , Wei CHEN , Hongshan KE , Fanlong ZENG , Yibo LEI , Anyang LI , Wenyuan WANG . Synthesis and bonding analysis of low-coordinate Fe and Cr complexes with ultra-bulky silylamino groups. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1285-1293. doi: 10.11862/CJIC.20250095
20. [20]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275

Get Citation

PDF

XML

Metrics

PDF Downloads(468)
Abstract views(1454)
HTML views(173)

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