Advances in Free-Radical Promoted C(sp3)—C(sp3) Bond Conversion

doi:10.6023/cjoc202108043

Abstract

Efficient C—C bond conversion might bring innovation to clean energy and circular economy. In the past several decades, developments of relatively chemical active carbon-carbon multibond conversion have been made. However, the research progress on effective functionalization of inert C(sp³)—C(sp³) bond is heavy going. The advances in this area from a free-radical chemistry point of view are summarized, which can help researchers who are interested in this topic to understand it quickly. The progesses as well as the corresponding mechanisms for free-radical promoted selective cleavage of saturated C—C bonds in alcohols and ethers, amines, aryl alkanes and simple alkanes are demonstrated. In each part, the explorations are depicted according to the initiating manners such as thermochemistry, photochemistry and electrochemistry.

Key words: free-radical chemistry, C—C bond activation, photochemistry, electrochemistry, alcohol and ether, amine, aryl alkane, simple alkane

Cite this article

Jintao Wu, Zhongquan Liu. Advances in Free-Radical Promoted C(sp³)—C(sp³) Bond Conversion[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 16-32.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 62

Scheme 1. Main pathway of C(sp3)—C(sp3) radical breaking in tertiary alcohols

Scheme 2. Main method for metal ion to promote the oxidation and ring opening of 1-methoxycyclopropanol

Scheme 3. Reaction mechanism of oxidation ring opening of phenyl cyclopropanol

Scheme 4. Intramolecular ring-opening and cyclization of cyclopropanols

Scheme 5. Synthesis mechanism of γ-carbonyl benzoquinone

Scheme 6. Silver-catalyzed ring-opening strategy for the synthesis of γ-fluorinated ketones

Scheme 7. Plausible mechanism of the synthesis of γ-fluorinated ketones

Scheme 8. Manganese-catalyzed oxidative azidation of cyclobutanols

Scheme 9. Proposed reaction mechanism of azidation of cyclobutanols

Scheme 10. Manganese-catalyzed oxidative ring-opening cyanation of cyclobutanols

Scheme 11. Oxidative C(OH)—C bond cleavage of secondary alcohols to acids

Scheme 12. Nitrogen dioxide catalyzed aerobic oxidative cleavage of C(OH)—C bond of secondary alcohols to acids

Scheme 13. Plausible reaction pathway for the aerobic oxidative cleavage and functionalization of C(OH)—C bond

Scheme 14. Aerobic oxidative cleavage and esterification of C(OH)—C bond

Scheme 15. Metal-free chemoselective oxidative dehomologation of primary alcohols

Scheme 16. Successive C(sp3)—C(sp3) bond cleavage in primary alcohols to access esters

Scheme 17. Possible reaction pathway of co-nc-900 catalyst for catalytic oxidation of primary alcohol and continuous cleavage of C—C bond to ester

Scheme 18. Photocatalyzed ring opening fluorination of cyclopropanols

Scheme 19. Proposed mechanism for photocatalyzed site-selective β-fluorination

Scheme 20. Synthesis of 1,8-dicarbonyl compounds

Scheme 21. Catalytic ring-opening of cyclic alcohols enabled by PCET activation of strong O—H bond

Scheme 22. Possible mechanism of catalytic ring-opening of cyclic alcohols via PCET

Scheme 23. Selective C(sp3)—C(sp3) bond cleavage and alkynylation of linear alcohols

Scheme 24. Plausible mechanism of selective C(sp3)—C(sp3) bond cleavage alkynylation of linear alcohols

Scheme 25. Photocatalytic C(sp3)—C(sp3) bond cleavage and amination of 2-methylcyclohexanol

Scheme 26. Proposed mechanism for the cleavage and amination of 2-methylcyclohexanol

Scheme 27. Photocatalytic isomerization of 2-methylcyclo- hexanol

Scheme 28. Selective photocatalytic C(sp3)—C(sp3) bond cleavage with vanadium complexes

Scheme 29. Cleavage of C(sp3)—C(sp3) bonds in primary alcohols for heteroaryl C—H alkylation

Scheme 30. Possible mechanism of cleavage of C(sp3)—C(sp3) bonds in primary alcohols for heteroaryl C—H alkylation

Scheme 31. Electrocatalytic oxidative cleavage by electrogenerated periodate

Scheme 32. Copper-catalyzed aerobic oxidative cleavage of C(sp3)—C(sp3) bond of dioxane

Scheme 33. Mechanism of copper-catalyzed aerobic oxidative cleavage of C(sp3)—C(sp3) bond of dioxane

Scheme 34. Deconstructive fluorination of cyclic amines by C(sp3)—C(sp3) bond selective cleavage

Scheme 35. Possible mechanism of deconstructive fluorination of cyclic amines by C(sp3)—C(sp3) bond selective cleavage

Scheme 36. Possible mechanism of deconstructive halogenation of cyclic amines by C(sp3)—C(sp3) bond selective cleavage

Scheme 37. Practical catalytic cleavage of C(sp3)—C(sp3) bond in amines

Scheme 38. Selective cleavage of the C—C/C—N bonds of piperidines promoted by tBuONO

Scheme 39. Proposed mechanism accounting for the formation of N-nitroso esters

Scheme 40. Tunable functionalization of saturated C—C bond of N,N'-diarylpiperazines

Scheme 41. Aerobic oxidative C(sp3)—C(sp3) bond cleavage of secondary amines

Scheme 42. Proposed mechanism for C(sp3)—C(sp3) bond cleavage

Scheme 43. Photocatalytic C(sp3)—C(sp3) bond breaking and polymerization of 1,2-diamine

Scheme 44. Mechanism of photocatalytic oxidative C(sp3)—C(sp3) cleavage of diamines

Scheme 45. [3+2] annulation of various arylamines

Scheme 46. Selective C(sp3)—C(sp3) cleavage/alkynylation of cycloalkylamides

Scheme 47. Electro-oxidation scission of 1,2-diaminocyclo- hexane using halogen ions as mediators

Scheme 48. Copper-catalyzed asymmetric aminocyanation of arylcyclopropanes

Scheme 49. Mechanism of synthesis of asymmetric γ-aminonitrile compounds

Scheme 50. Copper-catalyzed amination/azidation of arylcyclopropanes

Scheme 51. Reaction mechanism of site-specific oxidation of C(sp3)—C(sp3)/H Bonds in aryl alkanes

Scheme 52. Photochemical amination and fluorination of aryl cyclopropane by oxidative ring-opening

Scheme 53. Visible light mediated synthesis of β-chloro ketones from aryl cyclopropanes

Scheme 54. Reaction mechanism of synthesis of β-chloro ketones

Scheme 55. Visible-light-promoted diverse functionalization of C(sp3)—C(sp3) bond adjacent to an arene

Scheme 56. Plausible mechansim for deconstructive nitrogenation, peroxidation and chlorination by selective C(sp3)—C(sp3) bond cleavage

Scheme 57. Mechanism of electrochemical oxidation of ring opening of phenylcyclopropane

Scheme 58. Reactional pathways of electrochemical methoxylation of 1,2-di-(p-tertbutylphenyl)-ethane

Scheme 59. Electrochemical 1,3-difunctionalization of arylcyclopropanes

Scheme 60. Cyclohexane oxidized to produce adipic acid

Scheme 61. Cyclohexane to adipic acid by ozone and UV light

Scheme 62. Synthesis of adipic acid via organocatalytic direct oxidation of cyclohexane

References 55

[1]	For Selected reviews on C-C bond cleavage, see: (a) Drahl, M. A.; Manpadi, M.; Williams, L. J. Angew. Chem., Int. Ed. 2013, 52, 11222. doi: 10.1002/anie.v52.43 pmid: 28075115
	(b) Allpress, C. J.; Berreau, L. M. Coord. Chem. Rev. 2013, 257, 3005. doi: 10.1016/j.ccr.2013.06.001 pmid: 28075115
	(c) Dong, G. In C-C Bond Activation, Vol. 346, Springer, Berlin, 2013, pp. 195-232. pmid: 28075115
	(d) Chen, F.; Wang, T.; Jiao, N. Chem. Rev. 2014, 114, 8613. doi: 10.1021/cr400628s pmid: 28075115
	(e) Marek, I.; Masarwa, A.; Delaye, P.; Leibeling, M. Angew. Chem., Int. Ed. 2015, 54, 414. doi: 10.1002/anie.201405067 pmid: 28075115
	(f) Chen, P.; Billett, B. A.; Tsukamoto, T.; Dong, G. ACS Catal. 2017, 7, 1340. doi: 10.1021/acscatal.6b03210 pmid: 28075115
	(g) To, C. T.; Chan, K. S. Acc. Chem. Res. 2017, 50, 1702. doi: 10.1021/acs.accounts.7b00150 pmid: 28075115
	(h) Kim, D.; Park, W.; Jun, C. Chem. Rev. 2017, 117, 8977. doi: 10.1021/acs.chemrev.6b00554 pmid: 28075115
	(i) Fumagalli, G.; Stanton, S.; Bower, J. F. Chem. Rev. 2017, 117, 9404. doi: 10.1021/acs.chemrev.6b00599 pmid: 28075115
	(j) Song, F.; Gou, T.; Wang, B.-Q.; Shi, Z.-J. Chem. Soc. Rev. 2018, 47, 7078. doi: 10.1039/C8CS00253C pmid: 28075115
	(k) Sivaguru, P.; Wang, Z.; Zanoni, G.; Bi, X. Chem. Soc. Rev. 2019, 48, 2615. doi: 10.1039/C8CS00386F pmid: 28075115
	(l) Wang, B.; Perea, M. A.; Sarpong, R. Angew. Chem., Int. Ed. 2020, 59, 18898. doi: 10.1002/anie.v59.43 pmid: 28075115
	(m) Dai, P.-F.; Wang, H.; Cui, X.-C.; Qu, J.-P.; Kang, Y.-B. Org. Chem. Front. 2020, 7, 896. doi: 10.1039/C9QO01438A pmid: 28075115
	(n) Yu, X.-Y.; Chen, J.-R.; Xiao, W.-J. Chem. Rev. 2021, 121, 506. doi: 10.1021/acs.chemrev.0c00030 pmid: 28075115
	(o) Wang, J. H.; Blaszczyk, S. A.; Li, X.; Tang, W. Chem. Rev. 2021, 121, 110. doi: 10.1021/acs.chemrev.0c00160 pmid: 28075115
	(p) Murakami, M.; Ishida, N. Chem. Rev. 2021, 121, 264. doi: 10.1021/acs.chemrev.0c00569 pmid: 28075115
[2]	For selected recent reports on C(sp²)-C bond cleavage, see: (a) Xia, Y.; Lu, G.; Liu, P.; Dong, G. Nature 2016, 539, 546. doi: 10.1038/nature19849 pmid: 31097667
	(b) Yu, X.-Y.; Chen, J.-R.; Wang, P.-Z.; Yang, M.-N.; Liang, D.; Xiao, W.-J. Angew. Chem., Int. Ed. 2018, 57, 738. pmid: 31097667
	(c) Dauncey, E. M.; Morcillo, S. P.; Douglas, J. J.; Sheikh, N. S.; Leonori, D. Angew. Chem., Int. Ed. 2018, 57, 744. doi: 10.1002/anie.v57.3 pmid: 31097667
	(d) Liu, J.; Qiu, X.; Huang, X.; Luo, X.; Zhan, C.; Wei, J.; Pan, J.; Liang, Y.; Zhu, Y.; Qin, Q.; Song, S.; Jiao, N. Nat. Chem. 2019, 11, 7. pmid: 31097667
	(e) Smaligo, A. J.; Swain, M.; Quintana, J. C.; Tan, M. F.; Kim, D. A.; Kwon, O. Science 2019, 364, 681. doi: 10.1126/science.aaw4212 pmid: 31097667
	(f) Hicks, J.; Vasko, P.; Goicoechea, J. M.; Aldridge, S. J. Am. Chem. Soc. 2019, 141, 11000. doi: 10.1021/jacs.9b05925 pmid: 31097667
	(g) Liu, J.; Zhang, C.; Zhang, Z.; Wen, X.; Dou, X.; Wei, J.; Qiu, X.; Song, S.; Jiao, N. Science. 2020, 367, 281. doi: 10.1126/science.aay9501 pmid: 31097667
	(h) Swain, M.; Sadykhov, G.; Wang, R.; Kwon, O. Angew. Chem., Int. Ed. 2020, 59, 17565. doi: 10.1002/anie.v59.40 pmid: 31097667
	(i) Wang, G.; Guo, Y.; Wan, J. Chin. J. Org. Chem. 2020, 40, 645. (in Chinese) doi: 10.6023/cjoc201912018 pmid: 31097667
	(王国栋, 郭艳辉, 万结平, 有机化学, 2020, 40, 645.) doi: 10.6023/cjoc201912018 pmid: 31097667
	(j) Wang, M.; Wu, Y.; Yao, J.; Deng, L.; Pan, Y.; Huang, K.; Tang, H. Chin. J. Org. Chem. 2019, 39, 3223. (in Chinese) doi: 10.6023/cjoc201904051 pmid: 31097667
	(王毛锐, 吴雨峥, 姚健, 邓黎, 潘英明, 黄克斌, 唐海涛, 有机化学, 2019, 39, 3223.) doi: 10.6023/cjoc201904051 pmid: 31097667
	(k) Dai, H.; Wu, F.; Bai, D. Chin. J. Org. Chem. 2020, 40, 1423. (in Chinese) doi: 10.6023/cjoc202002035 pmid: 31097667
	(代洪雪, 吴芬, 白大昌, 有机化学, 2020, 40, 1423.) doi: 10.6023/cjoc202002035 pmid: 31097667
[3]	For selected reviews on cleavage of C-C bond in alcohols and/or ethers, see: (a) Ishida, N.; Murakami, M. Chem. Lett. 2017, 46, 1692. doi: 10.1246/cl.170834 pmid: 33085458
	(b) Jia, K.; Chen, Y. Chem. Commun. 2018, 54, 6105. doi: 10.1039/C8CC02642D pmid: 33085458
	(c) Wang, M.; Ma, J.; Liu, H.; Luo, N.; Zhao, Z.; Wang, F. ACS Catal. 2018, 8, 2129. doi: 10.1021/acscatal.7b03790 pmid: 33085458
	(d) Wu, X.; Zhu, C. Acc. Chem. Res. 2020, 53, 1620. doi: 10.1021/acs.accounts.0c00306 pmid: 33085458
	(e) McDonald, T. R.; Mills, L. R.; West, M. S.; Rousseaux, S. A. L. Chem. Rev. 2021, 121, 3. doi: 10.1021/acs.chemrev.0c00346 pmid: 33085458
	(f) Lutz, M. D. R.; Morandi, B. Chem. Rev. 2021, 121, 300. doi: 10.1021/acs.chemrev.0c00154 pmid: 33085458
[4]	Schaafsma, S. E.; Jorritsma, R.; Steinberg, H.; de Boer. T. J. Tetrahedron Lett. 1973, 11, 827.
[5]	Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka, K. Chem. Lett. 1991, 20, 1193. doi: 10.1246/cl.1991.1193
[6]	Iwasawa, N.; Funahnashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 22, 545. doi: 10.1246/cl.1993.545
[7]	Ilangovan, A.; Saravanakumar, S.; Malayappasamy, S. Org. Lett. 2013, 15, 4968. doi: 10.1021/ol402229m pmid: 24047506
[8]	Zhao, H.; Fan, X.; Yu, J.; Zhu, C. J. Am. Chem. Soc. 2015, 137, 3490. doi: 10.1021/jacs.5b00939
[9]	(a) Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2005, 44, 214. doi: 10.1002/(ISSN)1521-3773 pmid: 25379166
	(b) Rozen, S. Eur. J. Org. Chem. 2005, 2433. pmid: 25379166
	(b) Sanford, G. J. Fluorine Chem. 2007, 128, 90. doi: 10.1016/j.jfluchem.2006.10.019 pmid: 25379166
	(d) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305. doi: 10.1021/op700134j pmid: 25379166
	(e) Furuya, T.; Kuttruff, C. A.; Ritter, T. Curr. Opin. Drug Discovery Dev. 2008, 11, 803. pmid: 25379166
	(f) Hu, J.; Zhang, W.; Wang, F. Chem. Commun. 2009, 7465. pmid: 25379166
	(g) Furuya, T.; Klein, J. E. M. N.; Ritter, T. Synthesis 2010, 1804. pmid: 25379166
	(h) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470. doi: 10.1038/nature10108 pmid: 25379166
	(i) Hollingworth, C.; Gouverneur, V. Chem. Commun. 2012, 48, 2929. doi: 10.1039/c2cc16158c pmid: 25379166
	(j) Tredwell, M.; Gouverneur, V. Angew. Chem., Int. Ed. 2012, 51, 11426. doi: 10.1002/anie.201204687 pmid: 25379166
	(k) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214. doi: 10.1002/anie.v52.32 pmid: 25379166
	(l) Li, Y.; Wu, Y.; Li, G.-S.; Wang, X. S. Adv. Synth. Catal. 2014, 356, 1412. doi: 10.1002/adsc.v356.7 pmid: 25379166
	(m) Brooks, A. F.; Topczewski, J. J.; Ichiishi, N.; Sanford, M. S.; Scott, P. J. H. Chem. Sci. 2014, 5, 4545. pmid: 25379166
[10]	Ren, R.; Zhao, H.; Huan, L.; Zhu, C. Angew. Chem., Int. Ed. 2015, 54, 12692. doi: 10.1002/anie.201506578
[11]	(a) Brase, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188. doi: 10.1002/(ISSN)1521-3773
	(b) Lapointe, G.; Kapat, A.; Weidner, K.; Renaud, P. Pure Appl. Chem. 2012, 84, 1633. doi: 10.1351/PAC-CON-11-11-21
[12]	Ren, R.; Wu, Z.; Xu, Y.; Zhu, C. Angew. Chem., Int. Ed. 2016, 55, 2866. doi: 10.1002/anie.201510973
[13]	(a) Michelin, R. A.; Mozzon, M.; Bertani, R. Coord. Chem. Rev. 1996, 147, 299. doi: 10.1016/0010-8545(94)01128-1 pmid: 11996549
	(b) Kukushkin, V. Y.; Pombeiro, A. J. L. Chem. Rev. 2002, 102, 1771. pmid: 11996549
	(c) Kukushkin, V. Y.; Pombeiro, A. J. L. Inorg. Chim. Acta 2005, 358, 1. doi: 10.1016/j.ica.2004.04.029 pmid: 11996549
[14]	Wang, M.; Lu, J.; Li, L.; Li, H.; Liu, H.; Wang, F. J. Catal. 2017, 348, 160. doi: 10.1016/j.jcat.2017.02.017
[15]	(a) Wertz, S.; Studer, A. Green Chem. 2013, 15, 3116. doi: 10.1039/c3gc41459k pmid: 29707945
	(b) Cao, Q.; Dornan, L. M.; Rogan, L.; Hughes, N. L.; Muldoon, M. J. Chem. Commun. 2014, 50, 4524. doi: 10.1039/C3CC47081D pmid: 29707945
	(c) Nutting, M. J.; Rafiee, E.; Stahl, S. S. Chem. Rev. 2018, 118, 4834. doi: 10.1021/acs.chemrev.7b00763 pmid: 29707945
	(d) Shibuya, M.; Shibuta, T.; Fukuda, H.; Iwabuchi, Y. Org. Lett. 2012, 14, 5010. doi: 10.1021/ol3021435 pmid: 29707945
[16]	Liu, M.; Zhang, Z.; Song, J.; Liu, S.; Liu, H.; Han, B. Angew. Chem., Int. Ed. 2019, 58, 17393. doi: 10.1002/anie.v58.48
[17]	Liu, M.; Zhang, R.; Yan, J.; Liu, S.; Liu, H.; Liu, Z.; Wang, W.; He, Z.; Han, B. Chem 2020, 6, 3288. doi: 10.1016/j.chempr.2020.09.006
[18]	Kim, S. M.; Shin, H. Y.; Kim, D. W.; Yang, J. W. ChemSusChem 2016, 9, 241. doi: 10.1002/cssc.201501359
[19]	Luo, H.; Wang, L.; Shang, S.; Li, G.; Lv, Y.; Gao, S.; Dai, W. Angew. Chem., Int. Ed. 2020, 59, 19268. doi: 10.1002/anie.v59.43
[20]	Bloom, S.; Bume, D. D.; Pitts, C. R.; Lectka, T. Chem. Eur. J. 2015, 21, 8060. doi: 10.1002/chem.201501081
[21]	Ji, M.; Wu, Z.; Zhu, C. Chem. Commun. 2019, 55, 2368. doi: 10.1039/C9CC00378A
[22]	(a) Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076. doi: 10.1039/b602596j
	(b) Bellina, F.; Rossi, R. Tetrahedron 2006, 62, 7213. doi: 10.1016/j.tet.2006.05.024
[23]	Yayla, G. H.; Wang, H.; Tarantino, K. T.; Orbe, H. S.; Knowles, R. R. J. Am. Chem. Soc. 2016, 138, 10794. doi: 10.1021/jacs.6b06517
[24]	Jia, K.; Zhang, F.; Huang, H.; Chen, Y. J. Am. Chem. Soc. 2016, 138, 1514. doi: 10.1021/jacs.5b13066
[25]	Guo, J.; Hu, A.; Chen, Y.; Sun, J.; Tang, H.; Zuo, Z. W. Angew. Chem., Int. Ed. 2016, 128, 15319.
[26]	Ota, E.; Wang, H.; Frye, N. L.; Knowles, R. R. J. Am. Chem. Soc. 2019, 141, 1457. doi: 10.1021/jacs.8b12552
[27]	Gazi, S.; Ng, W. K. H.; Ganguly, R.; Moeljadi, A. M. P.; Hirao, H.; Soo, H. S. Chem. Sci. 2015, 6, 7130. doi: 10.1039/C5SC02923F
[28]	Wang, Y.; Yang, L.; Liu, S.; Huang, L.; Liu, Z. Q. Adv. Synth. Catal. 2019, 361, 4568. doi: 10.1002/adsc.v361.19
[29]	Shi, S.; Liang, Y.; Jiao, N. Chem. Rev. 2021, 121, 485. doi: 10.1021/acs.chemrev.0c00335 pmid: 33017147
[30]	Khan, F. N.; Jayakumar, R.; Pillai, C. N. J. Mol. Catal. A: Chem. 2003, 195, 139. doi: 10.1016/S1381-1169(02)00551-4
[31]	Liu, Z.; Zhao, L.; Shang, X.; Cui, Z. Org. Lett. 2012, 14, 3218. doi: 10.1021/ol301220s
[32]	For selected reviews on cleavage of C-C bond in amines, see: (a) Morcillo, S. P. Angew. Chem., Int. Ed. 2019, 58, 14044. doi: 10.1002/anie.v58.40
	(b) Sokolova, O. O.; Bower, J. F. Chem. Rev. 2021, 121, 80. doi: 10.1021/acs.chemrev.0c00166
[33]	Roque, J. B.; Kuroda, Y.; Göttemann, L. T.; Sarpong, R. Science 2018, 361, 171. doi: 10.1126/science.aat6365 pmid: 30002251
[34]	Roque, J. B.; Kuroda, Y.; Göttemann, L. T.; Sarpong, R. Nature 2018, 564, 244. doi: 10.1038/s41586-018-0700-3
[35]	Li, W.; Liu, W.; Leonard, D. K.; Rabeah, J.; Junge, K.; Brückner, A.; Beller, M. Angew. Chem., Int. Ed. 2019, 58, 10693. doi: 10.1002/anie.v58.31
[36]	He, Y.; Zheng, Z.; Liu, Y.; Qiao, J.; Zhang, X.; Fan, X. Org. Lett. 2019, 21, 1676. doi: 10.1021/acs.orglett.9b00226
[37]	He, K.; Zhang, T.; Zhang, S.; Sun, Z.; Zhang, Y.; Jia, X. Org. Lett. 2019, 21, 5030. doi: 10.1021/acs.orglett.9b01574
[38]	Yu, Y.; Zhang, Y.; Sun, C.; Shi, L.; Wang, W.; Li, H. J. Org. Chem. 2020, 85, 2725. doi: 10.1021/acs.joc.9b02919
[39]	Cai, S.; Zhao, X.; Wang, X.; Liu, Q.; Li, Z.; Wang, D. Z. Angew. Chem., Int. Ed. 2012, 51, 8050. doi: 10.1002/anie.v51.32
[40]	(a) Nguyen, T. H.; Morris, S. A.; Zheng, N. Adv. Synth. Catal. 2014, 356, 2831. doi: 10.1002/adsc.201400742 pmid: 28786686
	(b) Morris, S. A.; Wang, J.; Zheng, N. Acc. Chem. Res. 2016, 49, 1957. doi: 10.1021/acs.accounts.6b00263 pmid: 28786686
	(c) Cai, Y.; Wang, J.; Zhang, Y.; Li, Z.; Hu, D.; Zheng, N.; Chen, H. J. Am. Chem. Soc. 2017, 139, 12259. doi: 10.1021/jacs.7b06319 pmid: 28786686
[41]	Liu, Z.; Wu, S.; Chen, Y. ACS Catal. 2021, 11, 10565. doi: 10.1021/acscatal.1c02981
[42]	Shono, T.; Matsumura, Y.; Inoue, K. J. Am. Chem. Soc. 1984, 106, 6075. doi: 10.1021/ja00332a052
[43]	Yang, S.; Wang, L.; Zhang, H.; Liu, C.; Zhang, L.; Wang, X.; Zhang, G.; Li, Y.; Zhang, Q. ACS Catal. 2019, 9, 716. doi: 10.1021/acscatal.8b03768
[44]	Wang, L.; Wang, X.; Zhang, G.; Yang, S.; Li, Y.; Zhang, Q. Org. Chem. Front. 2019, 6, 2934. doi: 10.1039/C9QO00638A
[45]	Zhao, J.; Shen, T.; Sun, Z.; Wang, N.; Yang, L.; Wu, J.; You, H.; Liu, Z. Q. Org. Lett. 2021, 23, 4057. doi: 10.1021/acs.orglett.1c01303
[46]	(a) Rao, V. R.; Hixson, S. S. J. Am. Chem. Soc. 1979, 101, 6458. doi: 10.1021/ja00515a064
	(b) Hixson, S. S.; Garrett, D. W. J. Am. Chem. Soc. 1974, 96, 4872. doi: 10.1021/ja00822a026
[47]	Pitts, C. R.; Ling, B.; Snyder, J. A.; Bragg, A. E.; Lectka, T. J. Am. Chem. Soc. 2016, 138, 6598. doi: 10.1021/jacs.6b02838 pmid: 27136383
[48]	Petzold, D.; Singh, P.; Almqvist, F.; König, B. Angew. Chem., Int. Ed. 2019, 58, 8577. doi: 10.1002/anie.v58.25
[49]	Wang, Y.; Wang, N.; Zhao, J.; Sun, M.; You, H.; Fang, F.; Liu, Z. Q. ACS Catal. 2020, 10, 6603. doi: 10.1021/acscatal.0c01495
[50]	Shono, T.; Matsumura, Y. J. Org. Chem. 1970, 35, 4157. doi: 10.1021/jo00837a604
[51]	Zollinger, D.; Griesbach, U.; Putter, H.; Comninellis, C. Electrochem. Commun. 2004, 6, 605. doi: 10.1016/j.elecom.2004.04.014
[52]	Peng, P.; Yan, X.; Zhang, K.; Liu, Z.; Zeng, L.; Chen, Y.; Zhang, H.; Lei, A. Nat. Commun. 2021, 12, 3075. doi: 10.1038/s41467-021-23401-8 pmid: 34031421
[53]	Ishii, Y.; Iwahama, T; Sakaguchi, S.; Nakayama, K.; Nishiyama, Y. J. Org. Chem. 1996, 61, 4520. doi: 10.1021/jo951970l
[54]	Hwang, K. C.; Sagadevan, A. Science 2014, 346, 1495. doi: 10.1126/science.1259684 pmid: 25525242
[55]	Matsumoto, Y.; Kuriyama, M.; Yamamoto, K.; Nishida, K.; Onomura, O. Org. Process Res. Dev. 2018, 22, 1312. doi: 10.1021/acs.oprd.8b00196

自由基化学促进的饱和碳碳单键转化研究进展

Advances in Free-Radical Promoted C(sp³)—C(sp³) Bond Conversion

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 62

References 55

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jian Zhang, Wanjie Liang, Yi Yang, Fachao Yan, Hui Liu. Regiocontrollable Difunctionalization of N-Allenamines [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 335-348.
[2]	Yong Zhang, Zhigao Tian, Lin Huang, Qiufei Hou, Honghong Fan, Wanqiang Wang. Application of α-Cyanohydrin Methanesulfonates for the Synthesis of α-Aminonitriles [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 561-572.
[3]	Weizhong Ding, Bingwen Zhang, Yanqing Xue, Yuqi Lin, Zhijun Tang, Jing Wang, Wenchao Yang, Xiaofeng Wang, Wen Liu. A New Polyketide from Fusarium graminearum [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3319-3322.
[4]	Min Xi, Chao Duan, Jie Chi, Tian Fu, Xiaolong Su, Hongshe Wang. An Efficient and Rapid Synthesis of α-Aminonitriles via Strecker Reaction Catalyzed by Humic Acid [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3312-3318.
[5]	Boyu Yan, Jieliang Wu, Jinfei Deng, Dan Chen, Xiushen Ye, Qiuli Yao. Recent Progress in Light-Driven Direct Dehydroxylation and Derivation of Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3055-3066.
[6]	Xiangping Chen, Chenxiang Meng, Mengna Li, Shangmin Chu, Xinxin Zhu, Kai Xu, Lantao Liu, Tao Wang, Fenghua Zhang, Fei Li. Fe-Catalyzed Synthesis of Sulfide-Based Aromatic Primary Amines in Water Promoted by Sodium-Ascorbate [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2800-2807.
[7]	Rongbin Cai, Bing Li, Qi Zhou, Longyi Zhu, Jun Luo. Synthesis of 4,8,9,10-Tetrafunctionalized 2-Azaadamantanes and Their 2-Azaprotoadamantane Skeleton Isomers [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2217-2225.
[8]	Zeren Sun, Bingxin Zhai, Guangchao He, Hui Shen, Linya Chen, Shan Zhang, Yi Zou, Qihua Zhu, Yungen Xu. Synthesis and Anti-inflammatory Evaluation of Novel 1,2,3-Triazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2143-2155.
[9]	Yiwen Quan, Xinhui Jiang, Wenjun Li, Jian Wang. Access to α-Vinyl β-Alkynyl Enals via an Organocatalytic Deconjugation-Aldol Condensation Sequence [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2120-2125.
[10]	Zhou Zhang, Yu Guo, Jing Yang, Dan Wu, Jiaxin Wang, Xinyue Hong, Peijun Cai, Liangce Rong. Electrochemically Promoted Halogenation of Imidazoland-[1,2-a]pyridine with Dichloro(bromo)ethylene and Iodoform [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2104-2109.
[11]	Shengjie Jiang, Yang Wang, Xin Xu. Rare-Earth Metal Complexes-Catalyzed Dehydropolymerization of Methylamine-Boranes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1786-1791.
[12]	Yuyuan Liu, Yaqin Lei, Wen Yang, Wanxiang Zhao. Cobalt-Catalyzed Remote Hydroboration of Enamines [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1761-1771.
[13]	Maocai Xu, Jiazhuang Tian, Yanhua Yang, Gaozhang Gou, Fumin Li, Lin Shao, Kexin Chi. Reversible Mechanofluorochromic and Data Security Protection of a Triphenylamine-Based Difluoroboron Luminescent Compound [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1824-1831.
[14]	Linlin Du, Hua Zhang. Photochemical and Electrochemical Borylation Involving Aryl and Alkyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1726-1741.
[15]	Wei Wang, Zheyu Zhang, Xue Zhang, Haifeng Yu, Hui Luo, Dongyue Huo, Yupeng Xu, Xiaobo Zhao. Synthesis of Polysubstituted 2,3-Dihydropyridin-4(1H)-one in Water [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 742-750.