Citation: Qin Xiaofei, Liu Xiaoyan, Guo Caihong, Wu Haishun. Reaction Mechanisms of Carbonyl Compounds Hydrosilylation Catalyzed by Group VIII Transition Metal Complexes[J]. Chinese Journal of Organic Chemistry, ;2015, 36(1): 60-71. doi: 10.6023/cjoc201507037 shu

Reaction Mechanisms of Carbonyl Compounds Hydrosilylation Catalyzed by Group VIII Transition Metal Complexes

  • Corresponding author: Guo Caihong, sxgch2006@163.com
  • Received Date: 29 July 2015
    Revised Date: 21 September 2015

    Fund Project: the Shanxi Scholarship Council of China 2012-057the National Natural Science Foundation of China 21203115

Figures(16)

  • Hydrosilylation is an important reaction widely used in the silicone industries. Especially, the hydrosilylation of carbonyl compounds is of great value in synthetic organic chemistry. A variety of transition-metal complexes, such as iron, palladium, rhodium, ruthenium, platinum, etc., are now known to show catalytic activity in the hydrosilylation of ketones. Since organohydrosilanes may involve one, two, or three Si—H bonds in tertiary, secondary or primary silanes, respectively. The various types of compounds were produced in their reactions with the unsaturated substrates catalyzed by transition-metal complexes. In this paper, several reaction mechanisms of carbonyl compounds hydrosilylation catalyzed by group VIII transition metal complexes under different reaction conditions are mainly introduced. In particular, the new developments on mechanistic pathways for Rh, Ru, Fe and Ir catalytic systems from the type of reaction mechanism and the influence of reaction conditions are highlighted. In addition, some key intermediates and transition states, and their energetics are presented. Not only a summary of previous work is given, but also some ideas and inspirations are provided for future research.
  • 加载中
    1. [1]

      Levin, E.; Ivry, E.; Diesendruck, C. E.; Lemcoff, N. G. Chem. Rev. 2015, 115, 4607.  doi: 10.1021/cr400640e

    2. [2]

      Chakraborty, S.; Bhattacharya, P.; Dai, H.; Guan, H. Acc.Chem. Res. 2015, 48, 1995.  doi: 10.1021/acs.accounts.5b00055

    3. [3]

      Xu, D.-P.; Xiao, W.-J.; Peng, J.-J.; Li, J.-Y.; Bai, Y. Chin. J. Org. Chem. 2014, 34, 2195 (in Chinese).  doi: 10.6023/cjoc201406014
       

    4. [4]

      Wile, B. M.; Stradiotto, M. Chem.Commun. 2006, 39, 4104.

    5. [5]

      Carpentier, J-F.; Bette, V. Curr. Org. Chem. 2002, 6, 913.  doi: 10.2174/1385272023373851

    6. [6]

      Bauer, I.; Knölker, H-J. Chem.Rev. 2015, 115, 3170.  doi: 10.1021/cr500425u

    7. [7]

      Abbina, S.; Bian S.; Oian C.; Du, G. ACS Catal. 2013, 3, 678.  doi: 10.1021/cs300848h

    8. [8]

      Marciniec, B.; Guliński, J. Organomet. Chem. 1993, 446, 15.  doi: 10.1016/0022-328X(93)80030-F

    9. [9]

      Bleith, T.; Wadepohl, H.; Gade L. H. J. Am. Chem. Soc. 2015, 137, 2456.  doi: 10.1021/ja512986m

    10. [10]

      Sommer, L. H.; Pietrusza, E. W.; Whitmore, F. C. J. Am. Chem. Soc. 1947, 69, 188.

    11. [11]

      Ojima, I.; Nihonyanagi, M.; Nagai, Y. J. Chem. Soc., Chem. Commun. 1972, 16, 938a.

    12. [12]

      Lee, S.; Lim, C. W.; Song, C. E.; Kim, I. O. Tetrahedron: Asymmetry 1997, 8, 4027.  doi: 10.1016/S0957-4166(97)00554-5

    13. [13]

      Reyes, C.; Prock, A.; Giering, W. P. J. Organomet. Chem. 2003, 671, 13.  doi: 10.1016/S0022-328X(02)02221-0

    14. [14]

      Sawamura, M. Kuwano, R. Ito, Y. Angew. Chem. 1994, 106, 92.  doi: 10.1002/(ISSN)1521-3757

    15. [15]

      Ochida, A.; Sawamura, M. Chem. Asian J. 2007, 2, 609.  doi: 10.1002/(ISSN)1861-471X

    16. [16]

      Niyomura, O.; Iwasawa, T.; Sawada, N.; Tokunaga, M.; Obora, Y.; Tsuji, Y. Organometallics 2005, 24, 3468.  doi: 10.1021/om0503491

    17. [17]

      Nonnenmacher, M.; Kunz, D.; Rominger, F. Organometallics 2008, 27, 1561.  doi: 10.1021/om701196c

    18. [18]

      Liu, L.; Wang, F.; Shi, M. Organmetsllics 2009, 28, 4416.  doi: 10.1021/om900320c

    19. [19]

      Poyatos, M.; Maisse-François, A.; Bellemin-Laponnaz, S.; Gade, L. H. Organometallics 2006, 25, 2634.  doi: 10.1021/om060166u

    20. [20]

      Lugovoi, Y. M.; Tarasova, N. P.; Bourgeois, G.; Bryantseva, N. V.; Kostikov, V. V.; Filliatre, C.; Shostenko, A. G. React.Kinet. Catal. Lett. 1991, 43, 177.  doi: 10.1007/BF02075430

    21. [21]

      Ballestri, M.; Chatgilialoglu, C.; Clark, K. B.; Griller, D.; Giese, B.; Kopping, B. J. Org. Chem. 1991, 56, 678.  doi: 10.1021/jo00002a035

    22. [22]

      Barton, D. H. R.; Blundell, P.; Dorchak, J.; Jang, D. O.; Jaszberenyi, J. C. Tetrahedron 1991, 47, 8969.  doi: 10.1016/S0040-4020(01)86502-9

    23. [23]

      Shen, Z.; Khan, H. A.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2916.  doi: 10.1021/ja7109025

    24. [24]

      Hamasaka, G.; Kawamorita, S.; Ochida, A.; Akiyama, R.; Hara, K.; Fukuoka, A.; Asakura, K.; Chun, W. J.; Ohmiya, H.; Sawamura, M. Organometallics2008, 27, 6495.  doi: 10.1021/om800683g

    25. [25]

      Rubio, M.; Campos, J.; Carmona, E. Org. Lett. 2011, 13, 5236.  doi: 10.1021/ol202117t

    26. [26]

      Ojima, I.; Nihonyanagi, M.; Kogure, T.; Kumagai, M.; Horiuchi, S.; Nakatsugawa, K.; Nagai, Y. J. Organomet.Chem. 1975, 94, 449.  doi: 10.1016/S0022-328X(00)86954-5

    27. [27]

      Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1965, 87, 16.  doi: 10.1021/ja01079a004

    28. [28]

      Kolb, I.; Hetflejš, J. Collect. Czech. Chem. Commun. 1980, 45, 2808.  doi: 10.1135/cccc19802808

    29. [29]

      Reyes, C.; Prock, A.; Giering, W. P. Organometallics 2002, 21, 546.  doi: 10.1021/om0106682

    30. [30]

      Ojima, I.; Kogure, T.; Nagai, Y. Tetrahedron Lett. 1972, 13, 5035.  doi: 10.1016/S0040-4039(01)85162-5

    31. [31]

      Ojima, I.; Kogure, T. Organometallics1982, 1, 1390.  doi: 10.1021/om00070a024

    32. [32]

      Zheng, G. Z.; Chan, T. H. Organometallics 1995, 14, 70.  doi: 10.1021/om00001a015

    33. [33]

      Kolb, I.; Hetflejš, J. Collect. Czech. Chem. Commun.1980, 45, 2224.  doi: 10.1135/cccc19802224

    34. [34]

      Goikhman, R.; Milstein, D. Chem. Eur. J. 2005, 11, 2983.  doi: 10.1002/(ISSN)1521-3765

    35. [35]

      Gade, L. H.; César, V.; Bellemin-Laponnaz, S. Angew. Chem., Int. Ed. 2004, 43, 1014.  doi: 10.1002/(ISSN)1521-3773

    36. [36]

      Schneider, N.; Finger, M.; Haferkemper, C.; Bellemin-Laponnaz, S.; Hofmann, P.; Gade, L. H. Angew. Chem., Int. Ed. 2009, 48, 1609.  doi: 10.1002/anie.200804993

    37. [37]

      Schneider, N.; Finger, M.; Haferkemper, C.; Bellemin-Laponnaz, S.; Hofmann, P.; Gade, L. H. Chem. Eur. J. 2009, 15, 11515.  doi: 10.1002/chem.200901594

    38. [38]

      Gigler, P.; Bechlars, B.; Herrmann, W. A.; Kühn, F. E. J. Am. Chem. Soc. 2011, 133, 1589.  doi: 10.1021/ja110017c

    39. [39]

      Riener, K.; Högerl, M. P.; Gigler, P.; Kühn, F. E. ACSCatal. 2012, 2, 613.

    40. [40]

      Comte, V.; Balan, C.; Le, Gendre. P.; Moïse, C. Chem. Commun. 2007, 21, 713.

    41. [41]

      Eaborn, C.; Odell, K.; Pidcock, A. J. Organomet. Chem. 1973, 63, 93  doi: 10.1016/S0022-328X(73)80022-1

    42. [42]

      Corriu, R. J. P.; Moreau, J. J. E. J. Chem. Soc., Chem. Commun. 1973, 38.

    43. [43]

      Matsumoto, H.; Hoshino, Y.; Nagai, Y. Bull. Chem. Soc. Jpn. 1981, 54, 1279.  doi: 10.1246/bcsj.54.1279

    44. [44]

      Nagashima, H.; Suzuki, A.; Iura, T.; Ryu, K.; Matsubara, K. Organometallics2000, 19, 3579.  doi: 10.1021/om0003887

    45. [45]

      Semmelhack, M. F.; Misra, R. N. J. Org. Chem. 1982, 47, 2469.  doi: 10.1021/jo00133a045

    46. [46]

      Maifeld, S. V.; Miller, R. L.; Lee, D. Tetrahedron Lett. 2002, 43, 6363.  doi: 10.1016/S0040-4039(02)01385-0

    47. [47]

      Song, C.; Ma, C.; Ma, Y.; Feng, W.; Ma, S.; Chai, Q.; Andrus, M. B. Tetrahedron Lett. 2005, 46, 3241.  doi: 10.1016/j.tetlet.2005.03.026

    48. [48]

      Ochiai, M.; Hashimoto, H.; Tobita, H. Organometallics 2012, 31, 527.  doi: 10.1021/om2010854

    49. [49]

      Xie, H.; Lin, Z. Organometallics 2014, 33, 892.  doi: 10.1021/om401020g

    50. [50]

      Gutsulyak, D. V.; Vyboishchikov, S. F.; Nikonov, G. I. J. Am. Chem. Soc. 2010, 132, 5950.  doi: 10.1021/ja101583m

    51. [51]

      Yang, Y.-F.; Chung, L. W.; Zhang, X.; Houk, K. N.; Wu, Y.-D. J. Org. Chem. 2014, 79, 8856.  doi: 10.1021/jo501730n

    52. [52]

      Wang, J.; Huang, L.; Yang, X.; Wei, H. Organometallics 2015, 34, 212.  doi: 10.1021/om501071n

    53. [53]

      Brunner, H.; Fisch, K. Angew. Chem., Int. Ed. Engl. 1990, 29, 1131.  doi: 10.1002/(ISSN)1521-3773

    54. [54]

      Brunner, H.; Fisch, K. J. Organomet. Chem. 1991, 412, C11.  doi: 10.1016/0022-328X(91)86067-Z

    55. [55]

      Nishiyama, H.; Furuta, A. Chem. Commum. 2007, 760.

    56. [56]

      Muraoka, T.; Shimizu, Y.; Kobayashi, H.; Ueno, K.; Ogino, H. Organometallics 2010, 29, 5423.  doi: 10.1021/om100398u

    57. [57]

      Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440.  doi: 10.1021/ja961536g

    58. [58]

      Li, H.; Misal, Castro. L. C.; Zheng, J.; Roisnel, T.; Dorcet, V.; Sortais, J-B.; Darcel, C. Angew. Chem., Int. Ed. 2013, 52, 8045.  doi: 10.1002/anie.v52.31

    59. [59]

      Kennedy-Smith, J. J.; Nolin, K. A.; Gunterman, H. P.; Toste, F. D. J. Am. Chem. Soc. 2003, 125, 4056.  doi: 10.1021/ja029498q

    60. [60]

      Chung, L. W.; Lee, H. G.; Lin, Z.; Wu, Y.-D. J. Org. Chem. 2006, 71, 6000.  doi: 10.1021/jo060654b

    61. [61]

      Noronha, R. G.; Costa, P. J.; Romão, C. C.; Calhorda, M. J.; Fernandes, A. C. Organometallics 2009, 28, 6206.  doi: 10.1021/om9005627

    62. [62]

      Costa, P. J.; Romão, C. C.; Fernandes, A. C.; Royo, B.; Reis, P. M.; Calhorda, M. J. Chem. Eur. J. 2007, 13, 3934.  doi: 10.1002/(ISSN)1521-3765

    63. [63]

      Khalimon, A. Y.; Ignatov, S. K.; Simionescu, R.; Kuzmina, L. G.; Howard, J. A. K.; Nikonov, G. I. Inorg. Chem. 2012, 51, 754.  doi: 10.1021/ic201550a

    64. [64]

      Khalimon, A. Y.; Shirobokov, O. G.; Peterson, E.; Simionescu, R.; Kuzmina, L. G.; Howard, J. A. K. Nikonov, G. I. Inorg.Chem. 2012, 51, 4300.  doi: 10.1021/ic300010c

    65. [65]

      Shirobokov, O. G.; Kuzmina, L. G.; Nikonov, G. I. J. Am. Chem. Soc. 2011, 133, 6487.  doi: 10.1021/ja111748u

    66. [66]

      Bullock, R. M. Chem. Eur. J. 2004, 10, 2366.  doi: 10.1002/(ISSN)1521-3765

    67. [67]

      Bhattacharya, P.; Krause, J. A.; Guan, H. Organometallics2011, 30, 4720.  doi: 10.1021/om2005589

    68. [68]

      Wang, W.; Gu, P.; Wang, Y.; Wei, H. Organometallics 2014, 33, 847.  doi: 10.1021/om400634w

    69. [69]

      Apple, D. C.; Brady, K. A.; Chance, J. M.; Heard, N. E.; Nile, T. A. J. Mol. Catal. 1985, 29, 55.  doi: 10.1016/0304-5102(85)85130-0

    70. [70]

      Yang, J.; White, P. S.; Schauer, C. K.; Brookhart, M. Angew.Chem., Int. Ed. 2008, 47, 4141.  doi: 10.1002/(ISSN)1521-3773

    71. [71]

      Park, S.; Brookhart, M. Organometallics2010, 29, 6057.  doi: 10.1021/om100818y

    72. [72]

      Cheng, C.; Brookhart, M. Angew. Chem., Int. Ed. 2012, 51, 9422.  doi: 10.1002/anie.201205154

  • 加载中
    1. [1]

      Jing WUPuzhen HUIHuilin ZHENGPingchuan YUANChunfei WANGHui WANGXiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278

    2. [2]

      Anqi LIWenjing YANGXueming LIYanfong REN . Performance and mechanism of a foam Ti/FeCo-Fe2O3-CoFe2O4/SnO2-Sb anode for synergistic activation of peroxymonosulfate toward degradation of organic pollutants. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 944-958. doi: 10.11862/CJIC.20250323

    3. [3]

      Guowen Xing Guangjian Liu Le Chang . Five Types of Reactions of Carbonyl Oxonium Intermediates in University Organic Chemistry Teaching. University Chemistry, 2025, 40(4): 282-290. doi: 10.12461/PKU.DXHX202407058

    4. [4]

      Jiajie Li Xiaocong Ma Jufang Zheng Qiang Wan Xiaoshun Zhou Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117

    5. [5]

      Wanping Chen . Construction of Knowledge Logic and Discovery through Reasoning: Summarizing the Reaction Patterns of Reactive Metals with Oxygen. University Chemistry, 2026, 41(2): 95-102. doi: 10.12461/PKU.DXHX202503108

    6. [6]

      Mingyang MenJinghua WuGaozhan LiuJing ZhangNini ZhangXiayin Yao . Sulfide Solid Electrolyte Synthesized by Liquid Phase Approach and Application in All-Solid-State Lithium Batteries. Acta Physico-Chimica Sinica, 2025, 41(1): 100004-0. doi: 10.3866/PKU.WHXB202309019

    7. [7]

      Yerong Chen Bingbin Yang Xinglei He Yuqi Lin Keyin Ye . Enzyme-Directed Evolution Enables Bioconversion of Organosilicon Compounds. University Chemistry, 2025, 40(10): 121-129. doi: 10.12461/PKU.DXHX202411054

    8. [8]

      Yong Wang Yingying Zhao Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009

    9. [9]

      Yang Wang Shuangliang Liu Jianbo Zhao . Exploring the mechanism of Diels-Alder reaction: a computational chemistry experiment for undergraduate students. University Chemistry, 2026, 41(7): 257-265. doi: 10.12461/PKU.DXHX202504061

    10. [10]

      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

    11. [11]

      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

    12. [12]

      Zhi Chai Huashan Huang Xukai Shi Yujing Lan Zhentao Yuan Hong Yan . Wittig反应的立体选择性. University Chemistry, 2025, 40(8): 192-201. doi: 10.12461/PKU.DXHX202410046

    13. [13]

      Bolin Sun Jie Chen Ling Zhou . 乙烯型卤代烃的亲核取代反应. University Chemistry, 2025, 40(8): 152-157. doi: 10.12461/PKU.DXHX202410032

    14. [14]

      Hongting Yan Aili Feng Rongxiu Zhu Lei Liu Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010

    15. [15]

      Aili Feng Xin Lu Peng Liu Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072

    16. [16]

      Ling Fan Meili Pang Yeyun Zhang Yanmei Wang Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024

    17. [17]

      Jiabo Huang Quanxin Li Zhongyan Cao Li Dang Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172

    18. [18]

      Peng YUELiyao SHIJinglei CUIHuirong ZHANGYanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V2O5/TiO2 catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210

    19. [19]

      Qianlang Wang Jijun Sun Qian Chen Quanqin Zhao Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205

    20. [20]

      Zhuoming Liang Ming Chen Zhiwen Zheng Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By 1H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029

Metrics
  • PDF Downloads(0)
  • Abstract views(5510)
  • HTML views(857)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return