Citation: ZHONG Wei, YAN Hong. Reactivity of Unsaturated 16e Half-Sandwich Complex Cp^*Ir(S₂C₂B₁₀H₁₀) with ortho- and meta-Substituted Phenyl Azides[J]. Chinese Journal of Inorganic Chemistry, ;2015, 31(7): 1305-1314. doi: 10.11862/CJIC.2015.205 shu

Reactivity of Unsaturated 16e Half-Sandwich Complex Cp^Ir(S₂C₂B₁₀H₁₀) with ortho- and meta*-Substituted Phenyl Azides

ZHONG Wei ^1,2,, ,
YAN Hong ^2,,

1.
1 College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, China;
2.
2 State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, China

Corresponding author: ZHONG Wei, YAN Hong,
Received Date: 2 February 2015
Available Online: 2 June 2015
Fund Project: 国家自然科学基金(No.21301071)资助项目。 (No.21301071)

To test the influence of the position and electronic effect of the substituted group on the reaction system, detailed studies on the reactivity of unsaturated 16e half-sandwich complex Cp^*Ir(S₂C₂B₁₀H₁₀) (1) with ortho- and meta-substituted phenyl azides were performed. Reaction of 1 with ortho- and meta-substituted phenyl azides led to the formation of metal complexes in which C-H activation at ortho-position of aryl ring happened to construct a new C-S bond. These complexes were fully characterized by NMR (1H, 11B, 13C), FTIR, MS, elemental analysis and single crystal X-ray diffraction. Basing on the results of the same reaction system with irradiation, the radical mechanism for the formation of these complexes was proposed.
- half-sandwich complex;substituted phenyl azide;reactivity;mechanism
1. [1]
  [1] Cenini S, Gallo E, Caselli A, et al. Coord. Chem. Rev., 2006, 250(11/12):1234-1253
2. [2]
  [2] Cenini S, La Monica G. Inorg. Chim. Acta, 1976, 18:279-293
3. [3]
  [3] Cai S X, Glenn D J, Gee K R, et al. Bioconjugate Chem., 1993, 4(6):545-548
4. [4]
  [4] Plate M S. Photochem. Photobiol., 1997, 65(2):193-194
5. [5]
  [5] Cai S X, Glenn D J, Keana J F W. J. Org. Chem., 1992, 57(4): 1299-1304
6. [6]
  [6] Nahar P, Wali N M, Gandhi R P. Anal. Biochem., 2001, 294 (2):148-153
7. [7]
  [7] Clecak N J, Cox R J, Moreau W M. Polym. Eng. Sci., 1974, 14(7):491-493
8. [8]
  [8] Eikey R A, Abu-Omar M M. Coord. Chem. Rev., 2003, 243 (1/2):83-124
9. [9]
  [9] Wigley D E. Prog. Inorg. Chem., 2007, 42:239-482
10. [10]
  [10] Burrell A K, Steedman A J. Organometallics, 1997, 16(6): 1203-1208
11. [11]
  [11] Eikey R A, Khan S I, Abu-Omar M M. Angew. Chem., Int. Ed., 2002, 41(19):3591-3595
12. [12]
  [12] Mindiola D J, Hillhouse G L. Chem. Commun., 2002(17): 1840-1841
13. [13]
  [13] Bai G, Stephan D W. Angew. Chem., Int. Ed., 2007, 46(11): 1856-1859
14. [14]
  [14] Zhong W, Xie M S, Jiang Q B, et al. Chem. Commun., 2012, 48(15):2152-2154
15. [15]
  [15] Zhong W, Jiang Q B, Zhang Q, et al. Dalton Trans., 2014, 43 (13):4962-4968
16. [16]
  [16] Bae J Y, Park Y I, Ko J J, et al. Inorg. Chim. Acta, 1999, 289(1/2):141-148
17. [17]
  [17] Hebel D, Furlano D C, Phillips R S, et al. Bioorg. Med. Chem. Lett., 1992, 2(1):41-44
18. [18]
  [18] SMART Version 5.0, SAINT Version 6, SHELXTL Version 6.1 and SADABS Version 2.03. Bruker AXS Inc., Madison, Wisconsin, USA, 2000.
19. [19]
  [19] Sheldrick G M. SHELXS-97, Program for Crystal Structure Solution, University of Göttingen, Germany, 1997.
20. [20]
  [20] Sheldrick G M. SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.
21. [21]
  [21] Kumaran E, Sridevi V S, Leong W K. Organometallics, 2010, 29(23):6417-6421
22. [22]
  [22] Bae J Y, Park Y I, Ko J, et al. Inorg. Chim. Acta, 1999, 289 (1/2):141-148
23. [23]
  [23] Nomura M, Yagisawa T, Takayama C, et al. J. Organomet. Chem., 2000, 611(1/2):376-385
24. [24]
  [24] Hou Z M, Fujita A, Koizumi T, et al. Organometallics, 1999, 18(10):1979-1985
25. [25]
  [25] Sun K, Sachwani R, Richert K J, et al. Org. Lett., 2009, 11 (16):3598-3601
1. [1]
  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
2. [2]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
3. [3]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
4. [4]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
5. [5]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
6. [6]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
7. [7]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
8. [8]
  Yuting Zhang , Zhiqian Wang . Methods and Case Studies for In-Depth Learning of the Aldol Reaction Based on Its Reversible Nature. University Chemistry, 2024, 39(7): 377-380. doi: 10.3866/PKU.DXHX202311037
9. [9]
  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
10. [10]
  Tingbo Wang , Yao Luo , Bingyan Hu , Ruiyuan Liu , Jing Miao , Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082
11. [11]
  Daojuan Cheng , Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105
12. [12]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
13. [13]
  Xiaosong PU , Hangkai WU , Taohong LI , Huijuan LI , Shouqing LIU , Yuanbo HUANG , Xuemei LI . Adsorption performance and removal mechanism of Cd(Ⅱ) in water by magnesium modified carbon foam. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1537-1548. doi: 10.11862/CJIC.20240030
14. [14]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
15. [15]
  Yuejiao An , Wenxuan Liu , Yanfeng Zhang , Jianjun Zhang , Zhansheng Lu . Revealing Photoinduced Charge Transfer Mechanism of SnO₂/BiOBr S-Scheme Heterostructure for CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2407021-. doi: 10.3866/PKU.WHXB202407021
16. [16]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
17. [17]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
18. [18]
  Xiaohui Li , Ze Zhang , Jingyi Cui , Juanjuan Yin . Advanced Exploration and Practice of Teaching in the Experimental Course of Chemical Engineering Thermodynamics under the “High Order, Innovative, and Challenging” Framework. University Chemistry, 2024, 39(7): 368-376. doi: 10.3866/PKU.DXHX202311027
19. [19]
  Yonghui Wang , Weilin Chen , Yangguang Li . Knowledge Construction of “Solubility of Inorganic Substances” in Elemental Chemistry Teaching. University Chemistry, 2024, 39(4): 261-267. doi: 10.3866/PKU.DXHX202312102
20. [20]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(247)
HTML views(24)

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

Reactivity of Unsaturated 16e Half-Sandwich Complex Cp*Ir(S2C2B10H10) with ortho- and meta-Substituted Phenyl Azides

Metrics

通讯作者: 陈斌, bchen63@163.com

Reactivity of Unsaturated 16e Half-Sandwich Complex Cp^Ir(S₂C₂B₁₀H₁₀) with ortho- and meta*-Substituted Phenyl Azides