Chinese Journal of Organic Chemistry >
Research Progress in Transition-Metal-Free C—Si Bond Formation
Received date: 2023-07-16
Revised date: 2023-08-22
Online published: 2023-08-30
Supported by
National Key R&D Program of China(2022YFA1502902); National Nature Science Foundation of China(22222111); National Nature Science Foundation of China(21971198)
Organosilicons are widely used in many chemistry related fields. Given its important role, the chemical syntheses of organosilicon compounds have received considerable attention. Due to outstanding advantages in cost and environmental friendliness, transition-metal-free C—Si bond formation has been widely studied in the past decades and has been emerged as an important alternative to transition-metal-catalyzed C—Si cross-coupling. In this review, the recent developed methods of carbon-silicon bond formation under transition-metal-free conditions are summarized. The discussion is organized according to catalysts (acid catalysis, base catalysis, and radical initiation) and the types of C—Si bonds that formed. In addition, mechanistic discussions of representative reactions and a prospect for future development in this field are also briefly included.
Qiyang Li , Haiyan Zhang , Wenbo Liu . Research Progress in Transition-Metal-Free C—Si Bond Formation[J]. Chinese Journal of Organic Chemistry, 2023 , 43(10) : 3470 -3490 . DOI: 10.6023/cjoc202307017
| [1] | Brook M. A. Silicon in Organic, Organometallic, and Polymer Chemistry, Wiley, New York, 2000. |
| [2] | Franz A. K.; Wilson S. O. J. Med. Chem. 2013, 56, 388. |
| [3] | (a) Feng S.-Y.; Qu Z.-R.; Zhou Z.-K.; Chen J.-Y.; Gai L.-Z.; Lu H.; Chem. Commun. 2021, 57, 11689. |
| [3] | (b) Salgues B.; Sarkar R.; Fajri M. L.; Avalos-Quiroz Y. A.; Manick A.; Giorgi M.; Vanthuyne N.; Carissan Y.; Videlot- Ackermann C.; Ackermann J.; Canard G.; Parrain J.; Guennic B. L.; Jacquemin D.; Amatore M.; Commeiras L.; Zaborova E.; Fages F. J. Org. Chem. 2022, 87, 3276. |
| [4] | (a) Poole C. F. J. Chromatogr. A 2013, 1296, 2. |
| [4] | (b) Hsieh C.-Z.; Chung W.-H.; Ding W.-H. RSC Adv. 2021, 11, 23607. |
| [5] | (a) Mets?nen T. T.; Gallego D.; Szilvási T.; Driess M.; Oestreich M. Chem. Sci. 2015, 6, 7143. |
| [5] | (b) Bleith T.; Gade L. H. J. Am. Chem. Soc. 2016, 138, 6074. |
| [5] | (c) Park S.; Chang S. Angew. Chem., Int. Ed. 2017, 56, 7720. |
| [6] | Muramatsu W.; Yamamoto H. J. Am. Chem. Soc. 2021, 143, 6792. |
| [7] | Bellan A. B.; Knochel P. Angew. Chem., Int. Ed. 2019, 58, 1838. |
| [8] | McWilliams S. F.; Broere D. L. J.; Halliday C. J. V.; Bhutto S. M.; Mercado B. Q.; Holland P. L. Nature 2020, 584, 221. |
| [9] | (a) Verma V.; Koperniku A.; Edwards P. M.; Schafer L. L. Chem. Commun. 2022, 58, 9174. |
| [9] | (b) Kuci'nski K.; Stachowiak H.; Lewandowski D.; Gruszczy'nski M.; Lampasiak P.; Hreczycho G. J. Organomet. Chem. 2022, 961, 122127. |
| [9] | (c) Matsuoka K.; Komami N.; Kojima M.; Mita T.; Suzuki K.; Maeda S.; Yoshino T.; Matsunaga S. J. Am. Chem. Soc. 2021, 143, 103. |
| [10] | (a) Langkopf E.; Schinzer D. Chem. Rev. 1995, 95, 1375. |
| [10] | (b) Chatgilialoglu C.; Ferreri C.; Landais Y.; Timokhin V. I. Chem. Rev. 2018, 118, 6516. |
| [11] | Littleson M. M.; Campbell A. D.; Clarke A.; Dow M.; Ensor G.; Evans M. C.; Herring A.; Jackson B. A.; Jackson L. V.; Karlsson S.; Klauber D. J.; Legg D. H.; Leslie K. W.; Moravc?ík S?.; Parsons C. D.; Ronson T. O.; Meadows R. E. Org. Process Res. Dev. 2019, 23, 1407. |
| [12] | Komiyama T.; Minami Y.; Hiyama T. ACS Catal. 2017, 7, 631. |
| [13] | (a) Yang Y.-H.; Wang C.-Y. Sci. China Chem. 2015, 58, 1266. |
| [13] | (b) Lipke M. C.; Liberman-Martin A. L.; Tilley T. D. Angew. Chem., Int. Ed. 2017, 56, 2260. |
| [14] | Schuman D. P.; Liu W.-B.; Nesnas N.; Stoltz B. M. Organosilicon Chemistry: Novel Approaches and Reactions, Eds.: Hiyama, T.; Oestreich, M., Wiley-VCH Verlag GmbH & Co. KGaA, New York, 2019. |
| [15] | Tyagi A.; Yadav N.; Khan J.; Singh S.; Hazra C. K. Asian J. Org. Chem. 2021, 10, 334. |
| [16] | B?hr S.; Oestreich M. Angew. Chem., Int. Ed. 2017, 56, 52. |
| [17] | Gandhamsetty N.; Joung S.; Park S.-W.; Park S.; Chang S. J. Am. Chem. Soc. 2014, 136, 16780. |
| [18] | Gandhamsetty N.; Park S.; Chang S. J. Am. Chem. Soc. 2015, 137, 15176. |
| [19] | Hazra C. K.; Gandhamsetty N.; Park S.; Chang S. Nat. Commun. 2016, 7, 13431. |
| [20] | Gandhamsetty N. Park J.; Jeong J.; Park S.-W.; Park S.; Chang S. Angew. Chem., Int. Ed. 2015, 54, 6832. |
| [21] | Kim E.; Park S.; Chang S. Chem. Eur. J. 2018, 24, 5765. |
| [22] | Pérez M.; Hounjet L.; Caputo C.; Dobrovetsky R.; Stephan D. J. Am. Chem. Soc. 2013, 135, 18308. |
| [23] | Andrews R.; Chitnis S.; Stephan D. Chem. Commun. 2019, 55, 5599 |
| [24] | Parks D.; Blackwell J.; Piers W. J. Org. Chem. 2000, 65, 3090 |
| [25] | He T.; W, G.-Q.; Long P.-W.; Kemper S.; Irran E.; Klare H. F. T.; Oestreich M. Chem. Sci. 2021, 12, 569. |
| [26] | Fang H.-Q.; Xie K.X.; Kemper S.; Oestreich M. Angew. Chem., Int. Ed. 2021, 60, 8542. |
| [27] | Ma Y.-H.; Wang B.-L.; Zhang L.; Hou Z.-M. J. Am. Chem. Soc. 2016, 138, 3663. |
| [28] | Han Y.-X.; Zhang S.-T.; He J.-H.; Zhang Y.-T. J. Am. Chem. Soc. 2017, 139, 7399. |
| [29] | Han Y.-X.; Zhang S.; He J.-H.; Zhang Y.-T. ACS Catal. 2018, 8, 8765. |
| [30] | Zhang J.-B.; Park S.; Chang S. J. Am. Chem. Soc. 2018, 140, 13209. |
| [31] | Ma Y.-H.; Lou S.-J.; Luo G.; Luo Y.; Zhan G.; Nishiura M.; Luo Y.; Hou Z.-M. Angew. Chem., Int. Ed. 2018, 57, 15222. |
| [32] | Sasaki M.; Kondo Y. Org. Lett. 2015, 17, 848. |
| [33] | Toutov A.; Liu W.-B.; Betz K. N.; Fedorov A.; Stoltz B. M.; Grubbs R. H. Nature 2015, 518, 80. |
| [34] | Banerjee S.; Yang Y.-F.; Jenkins I. D.; Liang Y.; Toutov A. A.; Liu W.-B.; Schuman D. P.; Grubbs R. H.; Stoltz B. M.; Krenske E. H.; Houk K. N.; Zare R. N. J. Am. Chem. Soc. 2017, 139, 6880. |
| [35] | Liu W.-B.; Schuman D. P.; Yang Y.-F.; Toutov A. A.; Liang Y.; Klare H. F. T.; Nesnas N.; Oestreich M.; Blackmond D. G.; Virgil S. C.; Banerjee S.; Zare R. N.; Grubbs R. H.; Houk K. N.; Stoltz B. M. J. Am. Chem. Soc. 2017, 139, 6867. |
| [36] | Gu Y.-T.; Shen Y.-Y.; Zarate C.; Martin R. J. Am. Chem. Soc. 2019, 141, 127. |
| [37] | Toutov A. A.; Betz K. N.; Schuman D. P.; Liu W.-B.; Fedorov A.; Stoltz B. M.; Grubbs R. H. J. Am. Chem. Soc. 2017, 139, 1668. |
| [38] | Nozawa-Kumada K.; Inagi M.; Kondo Y. Asian J. Org. Chem. 2017, 6, 63. |
| [39] | Neil B.; Lucien F.; Fensterbank L.; Chauvier C. ACS Catal. 2021, 11, 13085. |
| [40] | Wang L.; Zhang T.; Sun W.; He Z.-Y.; Xia C.-G.; Lan Y.; Liu C. J. Am. Chem. Soc. 2017, 139, 5257. |
| [41] | Qi W.-Y.; Zhen J.-S.; Xu X.-H.; Du X.; Li Y.-H.; Yuan H.; Guan Y.-S.; We X.; Wang Z.-Y.; Liang G.-H.; Luo Y. Org. Lett. 2021, 23, 5988. |
| [42] | Liu X.-W.; Zarate C.; Martin R. Angew. Chem., Int. Ed. 2019, 58, 2064. |
| [43] | Mallick S.; Xu P.; Wgrthwein E.; Studer A. Angew. Chem., Int. Ed. 2019, 58, 283. |
| [44] | Oestreich M.; Hartmann E.; Mewald M. Chem. Rev. 2013, 113, 402. |
| [45] | Ito H.; Horit Y.; Yamamoto E. Chem. Commun. 2012, 48, 8006. |
| [46] | Morimasa Y.; Kabasawa K.; Ohmura T.; Suginome M. Asian J. Org. Chem. 2019, 8, 1092. |
| [47] | Nagao K.; Ohmiya H.; Sawamura M. Org. Lett. 2015, 17, 1304. |
| [48] | Gu Y.-T.; Duan Y.-Y.; Shen Y.-Y.; Martin R. Angew. Chem., Int. Ed. 2020, 59, 2061. |
| [49] | Jeong E.; Heo J.; Jin S.; Kim D.; Chang S. ACS Catal. 2022, 12, 4898. |
| [50] | Huo Y.-W.; Shen P.-P.; Duan W.-Z.; Zhen C.; Song C.; Ma Y.-D. Chin. Chem. Lett. 2018, 29, 1359. |
| [51] | Li T.-T.; Wu Y.-Z.; Duan W.-Z.; Ma Y.-D. RSC Adv. 2021, 11, 17860. |
| [52] | Xu P.; Würthwein E.; Daniliuc C.; Studer A. Angew. Chem., Int. Ed. 2017, 56, 13872. |
| [53] | Wang X.; Yu Z.-X.; Liu W.-B. Org. Lett. 2022, 24, 8735. |
| [54] | Shang X.-J.; Liu Z.-Q. Org. Biomol. Chem. 2016, 14, 7829. |
| [55] | Chatgilialoglu C.; Ferreri C.; Landais Y.; Timokhin V. I. Chem. Rev. 2018, 118, 6516. |
| [56] | Zhang X.-P.; Fang J.-K.; Cai C.; Lu G.-P. Chin. Chem. Lett. 2021, 32, 1280. |
| [57] | Li J.-S.; Wu J. ChemPhotoChem 2018, 2, 839. |
| [58] | Ren L.-Q.; Li N.; Ke J.; He C. Org. Chem. Front. 2022, 9, 6400. |
| [59] | Sakamoto R.; Nguyen B.; Maruoka K. Asian J. Org. Chem. 2018, 7, 1085. |
| [60] | Chang X.-H.; Wang Z.-L.; Zhao M.; Yang C.; Li J.-J.; Ma W.-W.; Xu Y.-H. Org. Lett. 2020, 22, 1326. |
| [61] | Leifert D.; Studer A. Org. Lett. 2015, 17, 386. |
| [62] | Studer A.; Curran D. P. Nat. Chem. 2014, 6, 765. |
| [63] | Lin Y.-M.; Lu G.-P.; Wang R.-K.; Yi W.-B. Org. Lett. 2017, 19, 1100. |
| [64] | Yang Y.; Song R.-J.; Li Y.; Ouyang X.-H.; Li J.-H.; He D.-L. Chem. Commun. 2018, 54, 1441. |
| [65] | Zhang C.; Pi J.-X.; Wang L.; Liu P.; Sun P.-P. Org. Biomol. Chem. 2018, 16, 9223. |
| [66] | Zhang T.-Y.; Zheng S.-H.; Kobayashi T.; Maekawa H. Org. Lett. 2021, 23, 7129. |
| [67] | Asgari P.; Hua Y.-D.; Bokka A.; Thiamsiri C.; Prasitwatcharakorn W.; Karedath A.; Chen X.; Sardar S.; Yum K.; Leem G.; Pierce B. S.; Nam K.; Gao J.-L.; Jeon J. Nat. Catal. 2019, 2, 164. |
| [68] | Buch F.; Brettar J.; Harder S. Angew. Chem., Int. Ed. 2006, 45, 2741. |
| [69] | Leich V.; Spaniol T.; Maron L.; Okuda J. Chem. Commun. 2014, 50, 2311 |
| [70] | Schuhknecht D.; Spaniol T.; Maron L.; Okuda J. Angew. Chem., Int. Ed. 2020, 59, 310. |
| [71] | Liu Z.-Z.; Shi X.-H.; Cheng J.-H. Dalton Trans. 2020, 49, 8340. |
| [72] | Zhao L.-X.; Shi X.-H.; Cheng J.-H. ACS Catal. 2021, 11, 2041. |
| [73] | Gong X.; Deng P.; Cheng J.-H. ChemCatChem 2022, 14, e202200060. |
| [74] | Li T.; McCabe K. N.; Maron L.; Leng X.-B.; Chen Y.-F. ACS Catal. 2021, 11, 6348. |
| [75] | Liu R.-X.; Liu X.-J.; Cheng T.-Y.; Chen Y.-F. Eur. J. Org. Chem. 2022, 1, e202101218. |
| [76] | Li T.; Liu R.-X.; Liu X.-J.; Chen Y.-F. Org. Lett. 2023, 25, 761 |
| [77] | Wang L.-L.; Li Y.-H.; Li Z.-F.; Kira M. Coord. Chem. Rev. 2022, 457, 214413. |
/
| 〈 |
|
〉 |
