Chinese Journal of Organic Chemistry >
X-Type Silyl Ligands Mediated C—H Functionalization Reactions
Received date: 2024-06-11
Revised date: 2024-07-18
Online published: 2024-08-26
Supported by
National Natural Science Foundation of China(22122102); National Natural Science Foundation of China(22271134); Guangdong Provincial Key Laboratory of Catalysis(2020B121201002); Guangdong Pearl River Talent Program(2019QN01Y628); Shenzhen Science and Technology Innovation Committee(RCJC20221008092723013); Shenzhen Science and Technology Innovation Committee(JCYJ20230807093104009)
The development of novel ligands for transition-metal (TM) catalysis holds significant importance. With the rapid evolution of organosilicon chemistry, summarizing the topic of X-type silyl ligands for TM catalysis is appealing and timely. The unique σ-donating characteristics and trans-effects of silyl ligands are explored, and their pivotal role in enhancing the reactivity and selectivity of C—H functionalization reactions is elucidated. Furthermore, valuable insights into future advancements in this field are also prospected, with the goal of inspiring new applications and perspectives in the realm of catalytic synthetic chemistry.
Jihui Gao , Chuan He . X-Type Silyl Ligands Mediated C—H Functionalization Reactions[J]. Chinese Journal of Organic Chemistry, 2025 , 45(2) : 641 -654 . DOI: 10.6023/cjoc202406014
| [1] | (a) Mayer, H. A.; Kaska, W. C. Chem. Rev. 1994, 94, 1239. |
| [1] | (b) Gordon, M. S.; Cundari, T. R. Coord. Chem. Rev. 1996, 147, 87. |
| [1] | (c) Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417. |
| [1] | (d) Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976. |
| [1] | (e) Souillart, L.; Cramer, N. Chem. Rev. 2015, 115, 9410. |
| [1] | (f) Obligacion, J. V.; Chirik, P. J. Nat. Rev. Chem. 2018, 2, 15. |
| [2] | (a) Straub, B. F. Angew. Chem., Int. Ed. 2010, 49, 7622. |
| [2] | (b) Takaya, J.; Iwasawa, N. Pincer and Pincer-Type Complexes: Applications in Organic Synthesis and Catalysis, Wiley-VCH, Weinheim, Germany, 2014, pp. 229-247. |
| [2] | (c) Fernández-Alvarez, F. J.; Lalrempuia, R.; Oro, L. A. Coord. Chem. Rev. 2017, 350, 49. |
| [3] | (a) Green, M. L. H. J. Organomet. Chem. 1995, 500, 127. |
| [3] | (b) Hara, N.; Semba, K.; Nakao, Y. ACS Catal. 2022, 12, 1626. |
| [4] | (a) Hein, F.; Pobloth, H. Z. Anorg. Allg. Chem. 1941, 248, 84. |
| [4] | (b) Piper, T. S.; Lemal, D.; Wilkinson, G. Naturwissenschaften 1956, 43, 129. |
| [5] | Whited, M. T.; Taylor, B. L. H. Comments Inorg. Chem. 2020, 40, 217. |
| [6] | (a) Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335. |
| [6] | (b) Haszeldine, R. N.; Parish, R. V.; Setchfield, J. H. J. Organomet. Chem. 1973, 57, 279. |
| [6] | (c) Aizenberg, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 6456. |
| [6] | (d) Sola, E. Pincer Compd. 2018, 401. |
| [7] | (a) Rabaa, H.; Saillard, J. Y.; Schubert, U. J. Organomet. Chem. 1987, 330, 397. |
| [7] | (b) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175. |
| [7] | (c) Corey, J. Y. Chem. Rev. 2016, 116, 11291. |
| [7] | (d) Fukumoto, Y.; Chatani, N. Organosilicon Chem. 2019, 171. |
| [8] | (a) Schubert, U. Adv. Organomet. Chem. 1990, 30, 151. |
| [8] | (b) Luo, X.-L.; Kubas, G. J.; Burns, C. J.; Bryan, J. C.; Unkefer, C. J. J. Am. Chem. Soc. 1995, 117, 1159. |
| [8] | (c) Corey, J. Y. Chem. Rev. 2011, 111, 863. |
| [9] | (a) Scherer, W.; Meixner, P.; Barquera-Lozada, J. E.; Hauf, C.; Obenhuber, A.; Brueck, A.; Wolstenholme, D. J.; Ruhland, K.; Leusser, D.; Stalke, D. Angew. Chem., Int. Ed. 2013, 52, 6092. |
| [9] | (b) Rios, P.; Fouilloux, H.; Vidossich, P.; Diez, J.; Lledos, A.; Conejero, S. Angew. Chem., Int. Ed. 2018, 57, 3217. |
| [9] | (c) Rios, P.; Fouilloux, H.; Diez, J.; Vidossich, P.; Lledos, A.; Conejero, S. Chem.-Eur. J. 2019, 25, 11346. |
| [9] | (d) Rios, P.; Conejero, S.; Fernandez, I. Chem.-Eur. J. 2022, 28, e202201920. |
| [10] | (a) Shimada, S.; Tanaka, M. Coord. Chem. Rev. 2006, 250, 991. |
| [10] | (b) Kuzu, I.; Krummenacher, I.; Meyer, J.; Armbruster, F.; Breher, F. Dalton Trans. 2008, 43, 5836. |
| [10] | (c) Simon, M.; Breher, F. Dalton Trans. 2017, 46, 7976. |
| [10] | (d) Kim, J. Bull. Korean Chem. Soc. 2022, 43, 538. |
| [10] | (e) Cabeza, J. A.; Garcia-Alvarez, P. Chem.-Eur. J. 2023, 29, e202203096. |
| [10] | (f) Gao, J.; Ge, Y.; He, C. Chem. Soc. Rev. 2024, 53, 4648. |
| [11] | Tilley, T. D. The Silicon-Heteroatom Bond, John Wiley & Sons Ltd, 1991, Chapter 9, p. 245. |
| [12] | (a) Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788. |
| [12] | (b) Hartwig, J. F. J. Am. Chem. Soc. 2016, 138, 2. |
| [12] | (c) He, C.; Whitehurst, W. G.; Gaunt, M. J. Chem 2019, 5, 1031. |
| [12] | (d) Dalton, T.; Faber, T.; Glorius, F. ACS Cent. Sci. 2021, 7, 245. |
| [12] | (e) Wang, S.; Yan, F.; Wang, L.; Zhu, L. Chin. J. Org. Chem. 2018, 38, 291 (in Chinese). |
| [12] | (汪珊, 严沣, 汪连生, 朱磊, 有机化学, 2018, 38, 291.) |
| [12] | (f) Wu, Y.; Shi, B. Chin. J. Org. Chem. 2020, 40, 3517 (in Chinese). |
| [12] | (吴勇杰, 史炳锋, 有机化学, 2020, 40, 3517.) |
| [12] | (g) Liu, X.; Kuang, C.; Su, C. Acta Chim. Sinica 2022, 80, 1135 (in Chinese). |
| [12] | (刘霞, 匡春香, 苏长会, 化学学报, 2022, 80, 1135.) |
| [13] | (a) Hartwig, J. F. Chem. Soc. Rev. 2011, 40, 1992. |
| [13] | (b) Ros, A.; Fernandez, R.; Lassaletta, J. M. Chem. Soc. Rev. 2014, 43, 3229. |
| [13] | (c) Xu, L.; Wang, G.; Zhang, S.; Wang, H.; Wang, L.; Liu, L.; Jiao, J.; Li, P. Tetrahedron 2017, 73, 7123. |
| [14] | MacLean, D. F.; McDonald, R.; Ferguson, M. J.; Caddell, A. J.; Turculet, L. Chem. Commun. 2008, 5146. |
| [15] | Fang, H.; Choe, Y.-K.; Li, Y.; Shimada, S. Chem.-Asian J. 2011, 6, 2512. |
| [16] | Takaya, J.; Ito, S.; Nomoto, H.; Saito, N.; Kirai, N.; Iwasawa, N. Chem. Commun. 2015, 51, 176625. |
| [17] | Komuro, T.; Mochizuki, D.; Hashimoto, H.; Tobita, H. Dalton Trans. 2022, 51, 9983. |
| [18] | (a) Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III, Science 2002, 295, 305. |
| [18] | (b) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390. |
| [18] | (c) Boller, T. M.; Murphy, J. M.; Hapke, M.; Ishiyama, T.; Miyaura, N.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 14263. |
| [19] | (a) Boebel, T. A.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 7534. |
| [19] | (b) Ishiyama, T.; Isou, H.; Kikuchi, T.; Miyaura, N. Chem. Commun. 2010, 46, 159. |
| [19] | (c) Crawford, K. M.; Ramseyer, T. R.; Daley, C. J. A.; Clark, T. B. Angew. Chem., Int. Ed. 2014, 53, 7589. |
| [20] | Ghaffari, B.; Preshlock, S. M.; Plattner, D. L.; Staples, R. J.; Maligres, P. E.; Krska, S. W.; Maleczka, R. E., Jr.; Smith, M. R., III, J. Am. Chem. Soc. 2014, 136, 14345. |
| [21] | Jiao, J.; Nie, W.; Song, P.; Li, P. Org. Biomol. Chem. 2021, 19, 355. |
| [22] | Takaya, J.; Kirai, N.; Iwasawa, N. J. Am. Chem. Soc. 2011, 133, 12980. |
| [23] | Kirai, N.; Iguchi, S.; Ito, T.; Takaya, J.; Iwasawa, N. Bull. Chem. Soc. Jpn. 2013, 86, 784. |
| [24] | Lee, C.-I.; Zhou, J.; Ozerov, O. V. J. Am. Chem. Soc. 2013, 135, 3560. |
| [25] | Lee, C.-I.; Shih, W.-C.; Zhou, J.; Reibenspies, J. H.; Ozerov, O. V. Angew. Chem., Int. Ed. 2015, 54, 14003. |
| [26] | Lee, C.-I.; Hirscher, N. A.; Zhou, J.; Bhuvanesh, N.; Ozerov, O. V. Organometallics 2015, 34, 3099. |
| [27] | Hyland, S. N.; Meck, E. A.; Tortosa, M.; Clark, T. B. Tetrahedron Lett. 2019, 60, 1096. |
| [28] | Dannatt, J. E.; Yadav, A.; Smith, M. R., III; Maleczka, R. E., Jr. Tetrahedron 2022, 109, 132578. |
| [29] | Jones, M. R.; Fast, C. D.; Schley, N. D. J. Am. Chem. Soc. 2020, 142, 6488. |
| [30] | Kawazu, R.; Torigoe, T.; Kuninobu, Y. Angew. Chem., Int. Ed. 2022, 61, e202202327. |
| [31] | (a) Cheng, C.; Hartwig, J. F. Chem. Rev. 2015, 115, 8946. |
| [31] | (b) Yuan, W.; He, C. Synthesis 2022, 54, 1939. |
| [31] | (c) Ge, Y.; Huang, X.; Ke, J.; He, C. Chem. Catal. 2022, 2, 2898. |
| [32] | Sangtrirutnugul, P.; Tilley, T. D. Organometallics 2007, 26, 5557. |
| [33] | Tobita, H.; Yamahira, N.; Ohta, K.; Komuro, T.; Okazaki, M. Pure Appl. Chem. 2008, 80, 1155. |
| [34] | Komuro, T.; Kitano, T.; Yamahira, N.; Ohta, K.; Okawara, S.; Mager, N.; Okazaki, M.; Tobita, H. Organometallics 2016, 35, 1209. |
| [35] | Kitano, T.; Komuro, T.; Ono, R.; Tobita, H. Organometallics 2017, 36, 2710. |
| [36] | Yang, B.; Tan, X.; Ge, Y.; Li, Y.; He, C. Org. Chem. Front. 2023, 10, 48620. |
| [37] | Yang, B.; Gao, J.; Tan, X.; Ge, Y.; He, C. Angew. Chem., Int. Ed. 2023, 62, e202307812. |
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