Chinese Journal of Organic Chemistry >
Recent Advances in Electrochemical-Promoted Unactivated C(sp3)—H Functionalization
Received date: 2023-09-22
Revised date: 2023-11-21
Online published: 2023-12-01
Supported by
Natural Science Foundation of Shandong Province(ZR2020MB005)
Organic electrosynthesis replaces traditional chemical oxidants or reductants with traceless electrons, which has the advantages of sustainability and easy to scale up. The functionalization of unactivated C(sp3)—H bond can directly introduce the target functional group into the molecules, avoiding pre-functionalization and possessing both atomic and step economies. With the development of organic electrosynthesis, electrochemical-promoted functionalization of unactivated C(sp3)—H bond has become one of the hotspots in organic synthesis. The functional groups are classified according to the types of functional groups, and the recent achievements related to the functionalization of unactivated C(sp3)—H bond are summarized, with emphasis on analyzing reaction advantages, substrate scope, and reaction mechanism. Finally, the current challenges and future development are briefly discussed.
Ruilin Gao , Lirong Wen , Weisi Guo . Recent Advances in Electrochemical-Promoted Unactivated C(sp3)—H Functionalization[J]. Chinese Journal of Organic Chemistry, 2024 , 44(3) : 892 -902 . DOI: 10.6023/cjoc202309024
| [1] | Faraday M. Ann. Phys. 1834, 47, 438. |
| [2] | Kolbe H. J. Prakt. Chem. 1847, 41, 138. |
| [3] | Yan M.; Kawamata Y.; Baran P. S. Chem. Rev. 2017, 117, 1323. |
| [4] | Xiong P.; Xu H.-C. Acc. Chem. Res. 2019, 52, 3339. |
| [5] | Yuan Y.; Yang Y.; Lei A. Chem. Soc. Rev. 2021, 50, 10058. |
| [6] | Cheng X.; Lei A.; Mei T.-S.; Xu H.-C.; Xu K.; Zeng C. CCS Chem. 2022, 4, 1120. |
| [7] | Tang H.-T.; Pan Y.-Z.; Pan Y.-M. Green Chem. 2023, 25, 8313. |
| [8] | Li Y.; Wen L.; Guo W. Chem. Soc. Rev. 2023, 52, 1168. |
| [9] | (a) He J.; Wasa M.; Chan K. S. L.; Shao Q.; Yu J.-Q. Chem. Rev. 2017, 117, 8754. |
| [9] | (b) Golden D. L.; Suh S.-E.; Stahl S. S. Nat. Rev. Chem. 2022, 6, 405. |
| [10] | Liu B.; Romine A. M.; Rubel C. Z.; Engle K. M.; Shi B.-F. Chem. Rev. 2021, 121, 14957. |
| [11] | White M. C.; Zhao J. J. Am. Chem. Soc. 2018, 140, 13988. |
| [12] | Kawamata Y.; Yan M.; Liu Z.; Bao D.-H.; Chen J.; Starr J. T.; Baran P. S. J. Am. Chem. Soc. 2017, 139, 7448. |
| [13] | Saito M.; Kawamata Y.; Meanwell M.; Navratil R.; Chiodi D.; Carlson E.; Hu P.; Chen L.; Udyavara S.; Kingston C.; Tanwar M.; Tyagi S.; McKillican B. P.; Gichinga M. G.; Schmidt M. A.; Eastgate M. D.; Lamberto M.; He C.; Tang T.; Malapit C. A.; Sigman M. S.; Minteer S. D.; Neuroc M. K.; Baran P. S. J. Am. Chem. Soc. 2021, 143, 7859. |
| [14] | (a) Che C. M.; Leung W. H. J. Chem. Soc., Chem. Commun. 1987, 18, 1376. |
| [14] | (b) Mack J. B. C.; Gipson J. D.; Bois J.; Sigman M. S. J. Am. Chem. Soc. 2017, 139, 9503. |
| [15] | Robinson S. G.; Mack J. B. C.; Alektiar S. N.; Bois J.; Sigman M. S. Org. Lett. 2020, 22, 7060. |
| [16] | (a) Huang Z.; Wang C.; Dong G. Angew. Chem., Int. Ed. 2016, 55, 5299. |
| [16] | (b) Chen F.-J.; Zhao S.; Hu F.; Chen K.; Zhang Q.; Zhang S.-Q.; Shi B.-F. Chem. Sci. 2013, 4, 4187. |
| [17] | Zhou L.; Lu W. Org. Lett. 2014, 16, 508. |
| [18] | Yang Q.-L.; Li Y.-Q.; Ma C.; Fang P.; Zhang X.-J.; Mei T.-S. J. Am. Chem. Soc. 2017, 139, 3293. |
| [19] | (a) Huang H.; Steiniger K. A.; Lambert T. H. J. Am. Chem. Soc. 2022, 144, 12567. |
| [19] | (b) Li P.; Zhang T.; Mushtaq M. A.; Wu S.; Xiang X.; Yan D. Chem. Rec. 2021, 21, 841. |
| [20] | Shen T.; Li Y.-L.; Lai L.-C.; Ye K.-Y.; Lambert T. Nature 2023, 614, 275. |
| [21] | (a) Thirumurugan P.; Matosiuk D.; Jozwiak K. Chem. Rev. 2013, 113, 4905. |
| [21] | (b) Meng G.; Guo T.; Ma T.; Zhang J.; Shen Y.; Sharpless K. B.; Dong J. Nature 2019, 574, 86. |
| [22] | Brase S.; Gil C.; Knepper K.; Zimmermann V. Angew. Chem., Int. Ed. 2005, 44, 5188. |
| [23] | (a) Sharma A.; Hartwig J. F. Nature 2015, 517, 600. |
| [23] | (b) Xia Y.; Wang L.; Studer A. Angew. Chem., Int. Ed. 2018, 57, 12940. |
| [24] | (a) Huang X.; Bergsten T. M.; Groves J. T. J. Am. Chem. Soc. 2015, 137, 5300. |
| [24] | (b) Suh S.-E.; Chen S.-J.; Mandal M.; Guzei I. A.; Cramer C. J.; Stahl S. S. J. Am. Chem. Soc. 2020, 142, 11388. |
| [25] | Niu L.; Jiang C.; Liang Y.; Liu D.; Bu F.; Shi R.; Chen H.; Chowdhury D.-A.; Lei A. J. Am. Chem. Soc. 2020, 142, 17693. |
| [26] | Meyer T. H.; Samanta R. C.; Vecchio A. D.; Ackermann L. Chem. Sci. 2021, 12, 2890. |
| [27] | (a) Hou Z.-W.; Liu D.-J.; Xiong P.; Lai X.-L.; Song J.; Xu H.-C. Angew. Chem., Int. Ed. 2021, 60, 2943. |
| [27] | (b) Wu J.; Zhou Y.; Zhou Y.; Chiang C.-W.; Lei A. ACS Catal. 2017, 7, 8320. |
| [28] | Zhang L.; Fu Y.; Liu C.; Sun M.; Cheng R.; Zhu W.; Qian X.; Ma Y.; Ye J. Nat. Commun. 2022, 13, 4138. |
| [29] | Crespi S.; Simeth N. A.; K?nig B. Nat. Rev. Chem. 2019, 3, 133. |
| [30] | Correia C. A.; Yang L.; Li C.-J. Org. Lett. 2011, 13, 4581. |
| [31] | Hu A.; Guo J.-J.; Pan H.; Zuo Z. Science 2018, 361, 668. |
| [32] | Xu P.; Chen P.-Y.; Xu H.-C. Angew. Chem., Int. Ed. 2020, 59, 14275. |
| [33] | Liu Y.; Shi B.; Liu Z.; Gao R.; Huang C.; Alhumade H.; Wang S.; Qi X.; Lei A. J. Am. Chem. Soc. 2021, 143, 20863. |
| [34] | Capaldo L.; Quadri L. L.; Merli D.; Ravelli D. Chem. Commun. 2021, 57, 4424. |
| [35] | Hagmann W. K. J. Med. Chem. 2008, 51, 4359. |
| [36] | West J. G.; Bedell T. A.; Sorensen E. J. Angew. Chem., Int. Ed. 2016, 55, 8923. |
| [37] | Liu W.; Huang X.; Cheng M.-J.; Nielsen R. J.; Goddard W. A.; Groves J. T. Science 2012, 337, 1322. |
| [38] | Takahira Y.; Chen M.; Kawamata Y.; Mykhailiuk P.; Nakamura H.; Peters B. K.; Reisberg S. H.; Li C.; Chen L.; Hoshikawa T.; Shibuguchid T.; Baran P. S. Synlett 2019, 30, 1178. |
| [39] | Zou L.; Wang X.; Xiang S.; Zheng W.; Lu Q. Angew. Chem., Int. Ed. 2023, e202301026. |
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