Citation: LIU Gui-Feng, YAN Hong. Reactivity of Half-Sandwich 16 Electron Compound CpCo (S₂C₂B₁₀H₁₀) with Ethyl Diazoacetate and Allenes[J]. Chinese Journal of Inorganic Chemistry, ;2017, 33(3): 487-492. doi: 10.11862/CJIC.2017.055 shu

Reactivity of Half-Sandwich 16 Electron Compound CpCo (S₂C₂B₁₀H₁₀) with Ethyl Diazoacetate and Allenes

LIU Gui-Feng ^1,2 ,
YAN Hong ^1,*,,

1.
State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China
2.
Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, China

Corresponding author: YAN Hong, hyan1965@nju.edu.cn
Received Date: 3 December 2016
Revised Date: 16 December 2016

Figures(4)

The three-component reactions of the 16 electron half-sandwich complex CpCo (S₂C₂B₁₀H₁₀) (Cp:cyclopentadienyl) with ethyl diazoacetate (EDA) and terminal allenes at ambient temperature lead to compounds 1 and 2. In 1 and 2, one EDA and one allene are inserted into Co-B bonds in a head-to-head mode making the hydrogen atom of the B (3)-H bond transform into the middle carbon of allene. One EDA molecule is also inserted into a Co-S bond to form a sulfide ylide. The new compounds 1 and 2 were characterized by NMR (¹H, ¹¹B, ¹³C), mass spectra, IR spectroscopy and elemental analysis, and their solid-state structures were further characterized by X-ray structural analysis.
- carborane,
- allene,
- ethyl diazoacetate,
- B-H activation
1. [1]
  Díaz-Requejo M M, Pérez P J. Chem. Rev., 2008, 108:3379-3394 doi: 10.1021/cr078364y
2. [2]
  Marek I, Simaan S, Masarwa A. Angew. Chem. Int. Ed., 2007, 46:7364-7376 doi: 10.1002/(ISSN)1521-3773
3. [3]
  Brackmann F, Meijere A. Chem. Rev., 2007, 107:4493-4537 doi: 10.1021/cr078376j
4. [4]
  Ma M, Wang J, et al. J. Am. Chem. Soc., 2005, 127:15016-15017 doi: 10.1021/ja055021d
5. [5]
  Lebel H, Marcoux J F, Charette A B, et al. Chem. Rev., 2003, 103:977-1050 doi: 10.1021/cr010007e
6. [6]
  Meng X, Wang F S, Jin G X, et al. Coord. Chem. Rev., 2010, 254:1260-1272 doi: 10.1016/j.ccr.2009.07.002
7. [7]
  Xu B H, Peng X Q, Yan H, et al. Chem. Eur. J., 2008, 14: 9347-9356
8. [8]
  Li Y G, Jiang Q B, Yan H, et al. Inorg. Chem., 2010, 49:4-6 doi: 10.1021/ic901970b
9. [9]
  Li Y G, Jiang Q B, Yan H, et al. Inorg. Chem., 2010, 49: 3911-3917 doi: 10.1021/ic1001804
10. [10]
  Liu G F, Hu J R, Yan H, et al. Inorg. Chem., 2011, 50: 4187-4194 doi: 10.1021/ic200333q
11. [11]
  Zhong W, Liu G F, Yan H, et al. Organometallics, 2012, 31: 6658-6668 doi: 10.1021/om300735d
12. [12]
  Zhang R, Zhu L, Yan, H, et al. J. Organomet. Chem., 2015, 798:152-159 doi: 10.1016/j.jorganchem.2015.06.013
13. [13]
  Wang Z J, Ye H D, Yan H, et al. J. Am. Chem. Soc., 2013, 135:11289-11298 doi: 10.1021/ja4047075
14. [14]
  Zhang R, Zhu L, Yan H, et al. J. Am. Chem. Soc., 2012, 134:10341-10344 doi: 10.1021/ja303334t
15. [15]
  Dai H M, Liu G F, Yan H, et al. Organometallics, 2015, 35: 1488-1496
16. [16]
  Liu G F, Yan H. Organometallics, 2015, 34:591-598 doi: 10.1021/om501016w
17. [17]
  Ma S. Chem. Rev., 2005, 105:2829-2872 doi: 10.1021/cr020024j
18. [18]
  Searle N E. Org. Synth., 1963, 4:424-426
19. [19]
  Buono G. Tetrahedron Lett., 1972, 13:3257-3259 doi: 10.1016/S0040-4039(01)94017-1
20. [20]
  Ma S, Hou H R, Wang G, et al. Synthesis, 2002, 12:1643-1645
21. [21]
  SAINT-Plus, Version 6.02, Bruker Analytical X-ray System, Madison, WI, 1999.
22. [22]
  Sheldrick G M. SADABS, Program for Empirical Absorption Correction, University of Göttingen, Germany, 1998.
23. [23]
  Sheldrick G M. SHELXS-97, Program for the Solution of Crystal Structures, University of Göttingen, Germany, 1990.
24. [24]
  Sheldrick, G M. SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.
1. [1]
  Shengwen XU , Longlong YANG , Houji CAO , Deshuang TU , Xing WEI , Changsheng LU , Hong YAN . Research progress on light-induced functionalization of polyhedral carborane clusters. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2187-2200. doi: 10.11862/CJIC.20250192
2. [2]
  Shuying Zhu , Shuting Wu , Ou Zheng . Improvement and Expansion of the Experiment for Determining the Rate Constant of the Saponification Reaction of Ethyl Acetate. University Chemistry, 2024, 39(4): 107-113. doi: 10.3866/PKU.DXHX202310117
3. [3]
  Ruitong Zhang , Zhiqiang Zeng , Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004
4. [4]
  Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177
5. [5]
  Zixuan Zhao , Miao Fan . “Carbon” with No “Ester”: A Boundless Journey of CO₂ Transformation. University Chemistry, 2025, 40(7): 213-217. doi: 10.12461/PKU.DXHX202409040
6. [6]
  Haotong Ma , Mingyu Heng , Yang Xu , Wei Bi , Yingchun Miao , Shuning Xiao . Synergistic carbon doping and Cu loading on boron nitride via microwave synthesis for enhanced atmospheric CO₂ photoreduction. Acta Physico-Chimica Sinica, 2025, 41(11): 100132-0. doi: 10.1016/j.actphy.2025.100132
7. [7]
  Hailang JIA , Yujie LU , Pengcheng JI . Preparation and properties of nitrogen and phosphorus co-doped graphene carbon aerogel supported ruthenium electrocatalyst for hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2327-2336. doi: 10.11862/CJIC.20250021
8. [8]
  Linhan Tian , Changsheng Lu . Discussion on Sextuple Bonding in Diatomic Motifs of Chromium Family Elements. University Chemistry, 2024, 39(8): 395-402. doi: 10.3866/PKU.DXHX202401056
9. [9]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
10. [10]
  Shiqian WEI , Xinyu TIAN , Hong LIU , Maoxia CHEN , Fan TANG , Qiang FAN , Weifeng FAN , Yu HU . Oxygen reduction reaction/oxygen evolution reaction catalytic performances of different active sites on nitrogen-doped graphene loaded with iron single atoms. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1776-1788. doi: 10.11862/CJIC.20250102
11. [11]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
12. [12]
  Zihan Cheng , Kai Jiang , Jun Jiang , Henggang Wang , Hengwei Lin . Achieving thermal-stimulus-responsive dynamic afterglow from carbon dots by singlet-triplet energy gap engineering through covalent fixation. Acta Physico-Chimica Sinica, 2026, 42(2): 100169-0. doi: 10.1016/j.actphy.2025.100169
13. [13]
  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
14. [14]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
15. [15]
  Kai CHEN , Fengshun WU , Shun XIAO , Jinbao ZHANG , Lihua ZHU . PtRu/nitrogen-doped carbon for electrocatalytic methanol oxidation and hydrogen evolution by water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1357-1367. doi: 10.11862/CJIC.20230350
16. [16]
  Yongwei ZHANG , Chuang ZHU , Wenbin WU , Yongyong MA , Heng YANG . Efficient hydrogen evolution reaction activity induced by ZnSe@nitrogen doped porous carbon heterojunction. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 650-660. doi: 10.11862/CJIC.20240386
17. [17]
  Yuecheng ZHANG , Fan YANG , Shiyu ZHANG , Chengjun MA , Rui TIAN , Xuehua SUN , Haoyu LI , Lingbo SUN , Hongyan MA . B-doped carbon quantum dots with long-afterglow room-temperature phosphorescence: Applications in information encryption and humidity sensing. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1361-1370. doi: 10.11862/CJIC.20240415
18. [18]
  Zhaomei LIU , Wenshi ZHONG , Jiaxin LI , Gengshen HU . Preparation of nitrogen-doped porous carbons with ultra-high surface areas for high-performance supercapacitors. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 677-685. doi: 10.11862/CJIC.20230404
19. [19]
  Zhuo Wang , Xue Bai , Kexin Zhang , Hongzhi Wang , Jiabao Dong , Yuan Gao , Bin Zhao . MOF-Templated Synthesis of Nitrogen-Doped Carbon for Enhanced Electrochemical Sodium Ion Storage and Removal. Acta Physico-Chimica Sinica, 2025, 41(3): 100026-0. doi: 10.3866/PKU.WHXB202405002
20. [20]
  Yunting Shang , Yue Dai , Jianxin Zhang , Nan Zhu , Yan Su . Something about RGO (Reduced Graphene Oxide). University Chemistry, 2024, 39(9): 273-278. doi: 10.3866/PKU.DXHX202306050

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1199)
HTML views(151)

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 Half-Sandwich 16 Electron Compound CpCo (S2C2B10H10) with Ethyl Diazoacetate and Allenes

Metrics

通讯作者: 陈斌, bchen63@163.com

Reactivity of Half-Sandwich 16 Electron Compound CpCo (S₂C₂B₁₀H₁₀) with Ethyl Diazoacetate and Allenes