十四族卡本衍生物: 一类重要的活性中间体
收稿日期: 2022-01-06
网络出版日期: 2022-02-24
基金资助
国家自然科学基金项目(21925603); 国家自然科学基金项目(21806167); 国家自然科学基金项目(22176191)
Carbone Derivatives of Group 14: A Class of Important Reactive Intermediates
Received date: 2022-01-06
Online published: 2022-02-24
Supported by
National Natural Science Foundation of China(21925603); National Natural Science Foundation of China(21806167); National Natural Science Foundation of China(22176191)
刘康 , 李斌 , 于吉攀 , 石伟群 . 十四族卡本衍生物: 一类重要的活性中间体[J]. 化学学报, 2022 , 80(3) : 373 -385 . DOI: 10.6023/A21120592
The pursuit of unusual bonding environments of carbon species with non-octet electronic configurations has been quite active in fundamental organic and theoretical chemistry for many decades. In this respect, a distinct carbone species has been successfully isolated recently and defined as “carbodicarbene” or “bent allene.” Carbone is an important active intermediate since the synthesis of radical, carbene and carbyne. This neutral two-coordinated central carbon atom possesses two sets of lone pair electrons, possessing strong coordination ability. The present review introduces the discovery, fundamental properties and coordination chemistry of carbone. Meanwhile, the application of its relevant complexes in catalysis is introduced.
| [1] | Yu, J.; Zhao, C.; Zhou, R.; Gao, W.; Wang, S.; Liu, K.; Chen, S.; Hu, K.; Mei, L.; Yuan, L.; Chai, Z.; Hu, H.; Shi, W. Chem. -Eur. J. 2020, 26, 16521. |
| [2] | Yang, W.; Zhang, M.; Chen, W.; Yang, X.; Feng, J. Chin. J. Org. Chem. 2020, 40, 4060. (in Chinese) |
| [2] | (杨文超, 张明明, 陈旺, 杨小虎, 冯建国, 有机化学, 2020, 40, 4060.) |
| [3] | Xiao, Y.-X.; Liu, Z.-Q. Acta Chim. Sinica 2019, 77, 874. (in Chinese) |
| [3] | (肖莹霞, 柳忠全, 化学学报, 2019, 77, 874.) |
| [4] | Zhang, Z.; Gong, L.; Zhou, X.-Y.; Yan, S.-S.; Li, J.; Yu, D.-G. Acta Chim. Sinica 2019, 77, 783. (in Chinese) |
| [4] | (张振, 龚莉, 周晓渝, 颜思顺, 李静, 余达刚, 化学学报, 2019, 77, 783.) |
| [5] | Guo, Y.; Xia, Z.; Liu, J.; Yu, J.; Yao, S.; Shi, W.; Hu, K.; Chen, S.; Wang, Y.; Li, A.; Driess, M.; Wang, W. J. Am. Chem. Soc. 2019, 141, 19252. |
| [6] | Chi, X.-W.; Wu, Q.-Y.; Lan, J.-H.; Wang, C.-Z.; Zhang, Q.; Chai, Z.-F.; Shi, W.-Q. Organometallics 2019, 38, 1963. |
| [7] | Li, A.-L.; Zhang, N.-X.; Wu, Q.-Y.; Wang, C.-Z.; Lan, J.-H.; Nie, C.-M.; Chai, Z.-F.; Shi, W.-Q. Organometallics 2021, 40, 1719. |
| [8] | Wang, Y.-M.; Wang, H.-W.; Liu, Z.-H. Acta Chim. Sinica 2021, 79, 1085. (in Chinese) |
| [8] | (王也铭, 王宏伟, 刘兆洪, 化学学报, 2021, 79, 1085.) |
| [9] | Zhang, J.-M.; Gao, J.; Feng, J.; Lu, T.; Du, D. Chin. J. Org. Chem. 2021, 41, 3792. (in Chinese) |
| [9] | (张建明, 高健, 冯捷, 陆涛, 杜鼎, 有机化学, 2021, 41, 3792.) |
| [10] | Zhang, H.-M.; Li, L.-Z.; Shen, F.-Q.; Cai, T.; Shen, R.-P. Chin. J. Org. Chem. 2020, 40, 873. (in Chinese) |
| [10] | (张慧苗, 李灵芝, 沈方旗, 蔡涛, 沈润溥, 有机化学, 2020, 40, 873.) |
| [11] | Arnett, C. H.; Agapie, T. J. Am. Chem. Soc. 2020, 142, 10059. |
| [12] | Frenking, G.; Hermann, M. Struct. Bond. 2016, 169, 131. |
| [13] | Yao, S.; Xiong, Y.; Driess, M. Acc. Chem. Res 2017, 50, 2026. |
| [14] | Frenking, G.; Tonner, R.; Klein, S.; Takagi, N.; Shimizu, T.; Krapp, A.; Pandey, K. K.; Parameswaran, P. Chem. Soc. Rev 2014, 43, 5106. |
| [15] | Frenking, G.; Hermann, M.; Andrada, D. M.; Holzmann, N. Chem. Soc. Rev. 2016, 45, 1129. |
| [16] | Frank, D. P.; Lies, B.; Jan, T.; Aleš, R.; Rudolph, W. Can. J. Chem. 2014, 92, 447. |
| [17] | Zhao, L.; Chai, C.; Petz, W.; Frenking, G. Molecules 2020, 25, 4943. |
| [18] | Yao, S.; Xiong, Y.; Saddington, A.; Driess, M. Chem. Commun. 2021, 57, 10139. |
| [19] | Vicente, J.; Singhal, A. R.; Jones, P. G. Organometallics 2002, 21, 5887. |
| [20] | Su, W.; Pan, S.; Sun, X.; Wang, S.; Zhao, L.; Frenking, G.; Zhu, C. Nat. Commun. 2018, 9, 4997. |
| [21] | Fang, W.; Pan, S.; Su, W.; Wang, S.; Zhao, L.; Frenking, G.; Zhu, C. CCS Chem. 2021, 3, 2324. |
| [22] | Su, W.; Pan, S.; Sun, X.; Zhao, L.; Frenking, G.; Zhu, C. Dalton Trans. 2019, 48, 16108. |
| [23] | Marrot, S.; Kato, T.; Gornitzka, H.; Baceiredo, A. Angew. Chem., Int. Ed. 2006, 45, 2598. |
| [24] | Lavallo, V.; Dyker, C. A.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2008, 47, 5411. |
| [25] | Christl, M.; Engels, B. Angew. Chem., Int. Ed. 2009, 48, 1538. |
| [26] | Lavallo, V.; Dyker, C. A.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2009, 48, 1540. |
| [27] | Melaimi, M.; Parameswaran, P.; Donnadieu, B.; Frenking, G.; Bertrand, G. Angew. Chem., Int. Ed. 2009, 48, 4792. |
| [28] | Pranckevicius, C.; Fan, L.; Stephan, D. W. J. Am. Chem. Soc. 2015, 137, 5582. |
| [29] | Dyker, C. A.; Lavallo, V.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2008, 47, 3206. |
| [30] | Chen, W.-C.; Hsu, Y.-C.; Lee, C.-Y.; Yap, G. P. A.; Ong, T.-G. Organometallics 2013, 32, 2435. |
| [31] | Hsu, Y.-C.; Shen, J.-S.; Lin, B.-C.; Chen, W.-C.; Chan, Y.-T.; Ching, W.-M.; Yap, G. P. A.; Hsu, C.-P.; Ong, T.-G. Angew. Chem., Int. Ed. 2015, 54, 2420. |
| [32] | Hsu, Y.-C.; Wang, V. C. C.; Au-Yeung, K.-C.; Tsai, C.-Y.; Chang, C.-C.; Lin, B.-C.; Chan, Y.-T.; Hsu, C.-P.; Yap, G. P. A.; Jurca, T.; Ong, T.-G. Angew. Chem., Int. Ed. 2018, 57, 4622. |
| [33] | Roberts, C. C.; Matías, D. M.; Goldfogel, M. J.; Meek, S. J. J. Am. Chem. Soc. 2015, 137, 6488. |
| [34] | Marcum, J. S.; Roberts, C. C.; Manan, R. S.; Cervarich, T. N.; Meek, S. J. J. Am. Chem. Soc. 2017, 139, 15580. |
| [35] | Pranckevicius, C.; Liu, L. L.; Bertrand, G.; Stephan, D. W. Angew. Chem., Int. Ed. 2016, 55, 5536. |
| [36] | El-Hellani, A.; Monot, J.; Tang, S.; Guillot, R.; Bour, C.; Gandon, V. Inorg. Chem. 2013, 52, 11493. |
| [37] | Aversa-Fleener, C. R.; Chang, D. K.; Liberman-Martin, A. L. Organometallics 2021, 40, 4050. |
| [38] | Chen, W.-C.; Shen, J.-S.; Jurca, T.; Peng, C.-J.; Lin, Y.-H.; Wang, Y.-P.; Shih, W.-C.; Yap, G. P. A.; Ong, T.-G. Angew. Chem., Int. Ed. 2015, 54, 15207. |
| [39] | Ishida, S.; Iwamoto, T.; Kabuto, C.; Kira, M. Nature 2003, 421, 725. |
| [40] | Mondal, K. C.; Roesky, H. W.; Schwarzer, M. C.; Frenking, G.; Niepötter, B.; Wolf, H.; Herbst-Irmer, R.; Stalke, D. Angew. Chem., Int. Ed. 2013, 52, 2963. |
| [41] | Xiong, Y.; Yao, S.; Tan, G.; Inoue, S.; Driess, M. J. Am. Chem. Soc. 2013, 135, 5004. |
| [42] | Xiong, Y.; Yao, S.; Müller, R.; Kaupp, M.; Driess, M. Angew. Chem., Int. Ed. 2015, 54, 10254. |
| [43] | Zhou, Y.-P.; Karni, M.; Yao, S.; Apeloig, Y.; Driess, M. Angew. Chem., Int. Ed. 2016, 55, 15096. |
| [44] | Yao, S.; Kostenko, A.; Xiong, Y.; Ruzicka, A.; Driess, M. J. Am. Chem. Soc. 2020, 142, 12608. |
| [45] | Wang, Y.; Karni, M.; Yao, S.; Kaushansky, A.; Apeloig, Y.; Driess, M. J. Am. Chem. Soc. 2019, 141, 12916. |
| [46] | Wang, Y.; Karni, M.; Yao, S.; Apeloig, Y.; Driess, M. J. Am. Chem. Soc. 2019, 141, 1655. |
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