Recent Advances in C—X Bond Metathesis Reactions

doi:10.6023/cjoc202202003

Abstract

Metathesis reaction, as a new type of chemical bond reorganization reaction, proved remarkably powerful for constructing inaccessible complex molecules by other methods in both industrial and academic settings, which greatly promotes the development of synthetic chemistry. However, most of the known metathesis reactions are mainly limited to the recombination reaction of multiple bonds, and the metathesis reactions of C—X single bonds are still in their infancy and face many opportunities and challenges. This is mainly due to the high bond energy of the C—X bonds, which is hard to break and reorganize. The progress of C—Si, C—P, C—S, C—I, C—O and C—N bonds metathesis reactions and their applications in organic synthesis are summarized according to the type of bonding.

Key words: chemical bond reorganization, C—X bond metathesis, heterocyclic compounds

Cite this article

Bangkui Yu, Hanmin Huang. Recent Advances in C—X Bond Metathesis Reactions[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2376-2389.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 33

Scheme 1. Types of C—X bond metathesis reactions

Scheme 2. Substituent redistribution of hydrosilanes

Scheme 3. C—Si/Si—H bond cross-metathesis of hydrosilanes

Scheme 4. Possible mechanism of cross-metathesis of hydrosilanes

Scheme 5. C—Si/Si—H bond cross-metathesis of cyclicgermylenes and hydrosilanes

Scheme 6. Ytterbium-catalyzed C—Si/Si—H bond cross-metathesis of silanes

Scheme 7. Generation and application of arylphosphonium salt

Scheme 8. Palladium-catalyzed C—P/C—P bond metathesis reaction

Scheme 9. Possible mechanism of C—P bond metathesis reaction

Scheme 10. Palladium-catalyzed functional group metathesis reaction

Scheme 11. Differentiation of C—P bond metathesis catalyzed by Pd and Ni

Scheme 12. Nickel-catalyzed C—P bond metathesis reaction

Scheme 13. Control experiments

Scheme 14. Palladium-catalyzed C—S/S—H bond metathesis reaction

Scheme 15. Possible mechanism of C—S bond metathesis reaction

Scheme 16. Nickel-catalyzed C—S/S—H bond metathesis reaction

Scheme 17. IL-catalyzed C—S/C—Br bond metathesis reaction

Scheme 18. Nickel-catalyzed functional group metathesis between aryl nitriles and aryl thioethers

Scheme 19. Nickel-catalyzed functional group metathesis between aryl thioethers and aryl electrophilies

Scheme 20. Iodonium metathesis reaction

Scheme 21. Copper-catalyzed C—I/C—H bond metathesis reaction

Scheme 22. Palladium-catalyzed C—I/C—Cl bond metathesis reaction

Scheme 23. Iron-catalyzed C—O/C—O bond ring-closing metathesis reaction

Scheme 24. IL-catalyzed C—O/C—O bond ring-closing metathesis reaction

Scheme 25. Amide bond metathesis

Scheme 26. Nickel-catalyzed C—N/N—H bond metathesis reaction of amide

Scheme 27. Palladium-catalyzed amine exchange of tertiary amines

Scheme 28. Possible mechanism of amine exchange

Scheme 29. Ruthenium-catalyzed C—N/N—H bond metathesis of amines

Scheme 30. Cobalt-catalyzed C—N/N—H bond metathesis of alkylamines

Scheme 31. Elementary reaction of C—N bond metathesis

Scheme 32. Palladium-catalyzed ring-closing reaction via C—N bond metathesis

Scheme 33. Possible mechanism of palladium-catalyzed C—N bond metathesis reaction

References 45

[1]	(a) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199. doi: 10.1021/cr0200872 pmid: 29714397
	(b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4490. doi: 10.1002/anie.200500369 pmid: 29714397
	(c) Higman, C. S.; Lummiss, J. A. M.; Fogg, D. E. Angew. Chem. Int. Ed. 2016, 55, 3552. doi: 10.1002/anie.201506846 pmid: 29714397
	(d) Grubbs, R. H.; Wenzel, A. G.; O'Leary, D. J.; Koshravi, E. Handbook of Metathesis, 2nd ed., Wiley, Weinheim, 2015, Vol. 1-3. pmid: 29714397
	(e) Ogba, M. O.; Warner, N. C.; O’Leary, D. J.; Grubbs, R. H. Chem. Soc. Rev. 2018, 47, 4510. doi: 10.1039/c8cs00027a pmid: 29714397
[2]	(a) Fürstner, A. In Handbook of Metathesis, Vol. 4, Ed.: Grubbs, R., Wiley-VCH, Weinheim, Germany, 2003, p. 432. pmid: 30335106
	(b) Zhang, W.; Moore, J. S. Adv. Synth. Catal. 2007, 349, 93. doi: 10.1002/adsc.200600476 pmid: 30335106
	(c) Yang, X.-X.; Zhang, Y.; Shao, Z.-Y. Chin. J. Org. Chem. 2010, 30, 968. (in Chinese) pmid: 30335106
	(杨晓霞, 张勇, 邵志宇, 有机化学, 2010, 30, 968.) pmid: 30335106
	(d) Ciaccia, M.; Di Stefano, S. Org. Biomol. Chem. 2015, 13, 646. doi: 10.1039/c4ob02110j pmid: 30335106
	(e) Ma, L.; Li, W.; Xi, H.; Bai, X.; Ma, E.; Yan, X.; Li, Z. Angew. Chem. Int. Ed. 2016, 55, 10410. doi: 10.1002/anie.201604349 pmid: 30335106
	(f) Becker, M. R.; Watson, R. B.; Schindler, C. S. Chem. Soc. Rev. 2018, 47, 7867. doi: 10.1039/c8cs00391b pmid: 30335106
[3]	(a) Cárdenas, D. J. Angew. Chem. Int. Ed. 1999, 38, 3018. doi: 10.1002/(SICI)1521-3773(19991018)38:20＜3018::AID-ANIE3018＞3.0.CO;2-F pmid: 11749317
	(b) Luh, T.-Y.; Leung, M.-K.; Wong, K.-T. Chem. Rev. 2000, 100, 3187. pmid: 11749317
	(c) Cárdenas, D. J. Angew. Chem. Int. Ed. 2003, 42, 384. doi: 10.1002/anie.200390123 pmid: 11749317
[4]	(a) Cecchetti, V.; Calderone, V.; Tabarrini, O.; Sabatini, S.; Filipponi, E.; Testai, L.; Spogli, R.; Martinotti, E.; Fravolini, A. J. Med. Chem. 2003, 46, 3670. pmid: 12904071
	(b) Katritzky, A. R. Chem. Rev. 2004, 104, 2125. doi: 10.1021/cr0406413 pmid: 12904071
	(c) Saracoglu, N. Top. Heterocycl. Chem. 2007, 11, 145. pmid: 12904071
	(d) Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Chem. Educ. 2013, 90, 1403. doi: 10.1021/ed4002317 pmid: 12904071
	(e) Nosova, E. V.; Lipunova, G. N.; Charushin, V. N.; Chupakhin, O. N. J. Fluorine Chem. 2018, 212, 51. doi: 10.1016/j.jfluchem.2018.05.012 pmid: 12904071
	(f) Meanwell, N. A.; Lolli, M. L. In Advances in Heterocyclic Chemistry, Vol. 134, 2021, pp. 2-320. pmid: 12904071
[5]	(a) Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596. doi: 10.1021/cr100347k pmid: 25157613
	(b) Wauters, I.; Debrouwer, W.; Stevens, C. V. Beilstein J. Org. Chem. 2014, 10, 1064. doi: 10.3762/bjoc.10.106 pmid: 25157613
	(c) Cornella, J.; Zarate, C.; Martin, R. Chem. Soc. Rev. 2014, 43, 8081. doi: 10.1039/c4cs00206g pmid: 25157613
	(d) Ouyang, K.; Hao, W.; Zhang, W.-X.; Xi, Z. Chem. Rev. 2015, 115, 12045. doi: 10.1021/acs.chemrev.5b00386 pmid: 25157613
	(e) Shen, C.; Zhang, P.; Sun, Q.; Bai, S.; Andy Hor, T. S.; Liu, X. Chem. Soc. Rev. 2015, 44, 291. doi: 10.1039/C4CS00239C pmid: 25157613
	(f) Wang, Q.; Su, Y.; Li, L.; Huang, H. Chem. Soc. Rev. 2016, 45, 1257. doi: 10.1039/C5CS00534E pmid: 25157613
	(g) Komiyama, T.; Minami, Y.; Hiyama, T. ACS Catal. 2017, 7, 631. doi: 10.1021/acscatal.6b02374 pmid: 25157613
	(h) Cai, B.-G.; Xuan, J.; Xiao, W.-J. Sci. Bull. 2019, 64, 337. doi: 10.1016/j.scib.2019.02.002 pmid: 25157613
	(i) Xiao, P.; Gao, L.; Song, Z. Chem. Eur. J. 2019, 25, 2407. doi: 10.1002/chem.201803803 pmid: 25157613
	(j) Chen, L.; Liu, X.-Y.; Zou, Y.-X. Adv. Synth. Catal. 2020, 362, 1724. doi: 10.1002/adsc.201901540 pmid: 25157613
	(k) Lou, J.; Wang, Q.; Wu, P.; Wang, H.; Zhou, Y.-G.; Yu, Z. Chem. Soc. Rev. 2020, 49, 4307. doi: 10.1039/C9CS00837C pmid: 25157613
[6]	(a) Hassner, A. In Topics in Heterocyclic Chemistry, Vol 12. Eds.: Hassner, A. Springer, Berlin, Heidelberg, 2008. pmid: 28585948
	(b) Wolfe, J. P. In Topics in Heterocyclic Chemistry, Vol 32. Eds.: Wolfe, J. P. Springer, Berlin, Heidelberg, 2013. pmid: 28585948
	(c) Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Chem. Rev. 2015, 115, 5301. doi: 10.1021/cr5006974 pmid: 28585948
	(d) Saito, A.; Tateishi, K. Heterocycles 2016, 92, 607. doi: 10.3987/REV-15-836 pmid: 28585948
	(e) Xuan, J.; Studer, A. Chem. Soc. Rev. 2017, 46, 4329. doi: 10.1039/c6cs00912c pmid: 28585948
[7]	(a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry, Wiley, New York, 2000.
	(b) Sore, H. F.; Galloway, W. R. J. D.; Spring, D. R. Chem. Soc. Rev. 2012, 41, 1845. doi: 10.1039/C1CS15181A
	(c) Komiyama, T.; Minami, Y.; Hiyama, T. ACS Catal. 2017, 7, 631. doi: 10.1021/acscatal.6b02374
[8]	(a) Curtis, M. D.; Epstein, P. S. Adv. Organomet. Chem. 1981, 19, 213. doi: 10.1016/S0022-328X(00)87774-8
	(b) Radu, N. S.; Hollander, F. J.; Tilley, T. D.; Rheingold, A. L. Chem. Commun. 1996, 21, 2459.
	(c) Castillo, I.; Tilley, T. D. Organometallics 2001, 20, 5598. doi: 10.1021/om010709u
	(d) Park, S.; Kim, B. G.; Göttker-Schnetmann, I.; Brookhart, M. ACS Catal. 2012, 2, 307. doi: 10.1021/cs200629t
	(e) Feigl, A.; Chiorescu, I.; Deller, K.; Heidsieck, S. U. H.; Buchner, M. R.; Karttunen, V.; Bockholt, A.; Genest, A.; Rösch, N.; Rieger, B. Chem.-Eur. J. 2013, 19, 12526. doi: 10.1002/chem.201203139
[9]	Ma, Y.; Zhang, L.; Luo, Y.; Nishiura, M.; Hou, Z. J. Am. Chem. Soc. 2017, 139, 12434. doi: 10.1021/jacs.7b08053
[10]	Rao, B.; Wang, L.; Kinjo, R. Angew. Chem. Int. Ed. 2019, 58, 231. doi: 10.1002/anie.201811574
[11]	Liu, X.; Xiang, L.; Louyriac, E.; Maron, L.; Leng, X.; Chen, Y. J. Am. Chem. Soc. 2019, 141, 138. doi: 10.1021/jacs.8b12138
[12]	(a) Guo, C.; Li, M.; Chen, J.; Luo, Y. Chem. Commun. 2020, 56, 117. doi: 10.1039/C9CC07493G
	(b) Liu, Z.; Shi, X.; Cheng, J. Dalton Trans. 2020, 49, 8340. doi: 10.1039/D0DT01158D
	(c) Li, T.; McCabe, K. N.; Maron, L.; Leng, X.; Chen, Y. ACS Catal. 2021, 11, 6348. doi: 10.1021/acscatal.1c00463
[13]	(a) Hartwig, J. F. Organotransition Metal Catalysis, Palgrave Macmillan, 2009, pp. 668-676. pmid: 17091932
	(b) Bertrand, G. Chem. Rev. 1994, 94, 1161. doi: 10.1021/cr00029a600 pmid: 17091932
	(c) Baumgartner, T.; Réau, R. Chem. Rev. 2006, 106, 4681. pmid: 17091932
	(d) Stolar, M.; Baumgartner, T. Chem. Asian J. 2014, 9, 1212. doi: 10.1002/asia.201301670 pmid: 17091932
[14]	(a) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. doi: 10.1021/om00084a019
	(b) Goodson, F. E.; Wallaw, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. doi: 10.1021/ja972554g
[15]	(a) Ziegler Jr., C. B.; Heck, R. F. J. Org. Chem. 1978, 43, 2941. doi: 10.1021/jo00409a001 pmid: 11500901
	(b) de la Torre, G.; Gouloumis, A.; Vázquez, P.; Torres, T. Angew. Chem. Int. Ed. 2001, 40, 2895. pmid: 11500901
	(c) Hwang, L. K.; Na, Y.; Lee, J.; Do, Y.; Chang, S. Angew. Chem. Int. Ed. 2005, 44, 6166. doi: 10.1002/anie.200501582 pmid: 11500901
[16]	Lian, Z.; Bhawal, B. N.; Yu, P.; Morandi, B. Science 2017, 356, 1059. doi: 10.1126/science.aam9041
[17]	Baba, K.; Masuya, Y.; Chatani, N.; Tobisu, M. Chem. Lett. 2017, 46, 1296. doi: 10.1246/cl.170581
[18]	Ho Lee, Y.; Morandi, B. Nat. Chem. 2018, 10, 1016. doi: 10.1038/s41557-018-0078-8
[19]	Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299. doi: 10.1038/nature13274
[20]	Fujimoto, H.; Kusano, M.; Kodama, T.; Tobisu, M. Org. Lett. 2019, 21, 4177. doi: 10.1021/acs.orglett.9b01355 pmid: 31117707
[21]	(a) Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832. doi: 10.1021/jm401375q
	(b) Boyd, D. A. Angew. Chem. Int. Ed. 2016, 55, 15486. doi: 10.1002/anie.201604615
	(c) Rahate, A. S.; Nemade, K. R.; Waghuley, S. A. Rev. Chem. Eng. 2013, 29, 471.
[22]	Sugahara, T.; Murakami, K.; Yorimitsu, H.; Osuka, A. Angew. Chem. Int. Ed. 2014, 53, 9329. doi: 10.1002/anie.201404355
[23]	Delcaillau, T.; Bismuto, A.; Lian, Z.; Morandi, B. Angew. Chem. Int. Ed. 2020, 59, 2110. doi: 10.1002/anie.201910436 pmid: 31829493
[24]	Liu, C.; Chen, D.; Fu, Y.; Wang, F.; Luo, J.; Huang, S. Org. Lett. 2020, 22, 5701. doi: 10.1021/acs.orglett.0c02089
[25]	Delcaillau, T.; Boehm, P.; Morandi, B. J. Am. Chem. Soc. 2021, 143, 3723. doi: 10.1021/jacs.1c00529 pmid: 33655746
[26]	Isshiki, R.; Kurosawa, M. B.; Muto, K.; Yamaguchi, J. J. Am. Chem. Soc. 2021, 143, 10333. doi: 10.1021/jacs.1c04215
[27]	Kasahara, T.; Jang, Y. J.; Racicot, L.; Panagopoulos, D.; Liang, S. H.; Ciufolini, M. A. Angew. Chem. Int. Ed. 2014, 53, 9637. doi: 10.1002/anie.201405594
[28]	Chung, R.; Vo, A.; Hein, J. E. ACS Catal. 2017, 7, 2505. doi: 10.1021/acscatal.6b03515
[29]	De La Higuera Macias, M.; Arndtsen, B. A. J. Am. Chem. Soc. 2018, 140, 10140. doi: 10.1021/jacs.8b06605
[30]	(a) Otera, J. Chem. Rev. 1993, 93, 1449. doi: 10.1021/cr00020a004
	(b) “Esters, Organic”: Riemenschneider, W.; Bolt, H. Ullmann's Encyclopedia of Industrial Chemistry, Electronic Release, Wiley- VCH, Weinheim, 2005.
	(c) Yu, C.; Huang, H.; Li, X.; Zhang, Y.; Wang, W. J. Am. Chem. Soc. 2016, 138, 6956. doi: 10.1021/jacs.6b03609
	(d) Lam, Y.-P.; Wang, X.; Tan, F.; Ng, W.-H.; Steve Tse, Y.-L.; Yeung, Y.-Y. ACS Catal. 2019, 9, 8083. doi: 10.1021/acscatal.9b01959
[31]	Biberger, T.; Makai, S.; Lian, Z.; Morandi, B. Angew. Chem. Int. Ed. 2018, 57, 6940. doi: 10.1002/anie.201802563 pmid: 29603569
[32]	Wang, H.; Zhao, Y.; Zhang, F.; Wu, Y.; Li, R.; Xiang, J.; Wang, Z.; Han, B.; Liu, Z. Angew. Chem. Int. Ed. 2020, 59, 11850. doi: 10.1002/anie.202004002
[33]	Vidal, J. L.; Wyper, O. M.; MacQuarrie, S. L.; Kerton, F. M. Eur. J. Org. Chem. 2021, 6052.
[34]	(a) Davidsen, S. K.; May, P. D.; Summers, J. B. J. Org. Chem. 1991, 56, 5482. doi: 10.1021/jo00018a059
	(b) Bon, E.; Bigg, D. C. H.; Bertrand, G. J. Org. Chem. 1994, 59, 4035. doi: 10.1021/jo00094a004
	(c) Greenberg, A.; Breneman, C. M.; Liebman, J. F. The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science, Wiley-VCH, Weinheim, 2002.
	(d) Mucsi, Z.; Chass, G. A.; Csizmadia, I. G. J. Phys. Chem. B 2008, 112, 7885. doi: 10.1021/jp8023292
[35]	(a) Eldred, S. E.; Stone, D. A.; Gellman, S. H.; Stahl, S. S. J. Am. Chem. Soc. 2003, 125, 3422. pmid: 19621957
	(b) Bell, C. M.; Kissounko, D. A.; Gellman, S. H.; Stahl, S. S. Angew. Chem. Int. Ed. 2007, 46, 761. pmid: 19621957
	(c) Stephenson, N. A.; Zhu, J.; Gellman, S. H.; Stahl, S. S. J. Am. Chem. Soc. 2009, 131, 10003. doi: 10.1021/ja8094262 pmid: 19621957
[36]	(a) Hie, L.; Fine Nathel, N. F.; Shah, T. K.; Baker, E. L.; Hong, X.; Yang, Y.-F.; Liu, P.; Houk, K. N.; Garg, N. K. Nature 2015, 524, 79. doi: 10.1038/nature14615 pmid: 27199089
	(b) Baker, E. L.; Yamano, M. M.; Zhou, Y.; Anthony, S. M.; Garg, N. K. Nat. Commun. 2016, 7, 11554. doi: 10.1038/ncomms11554 pmid: 27199089
[37]	Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. J. Med. Chem. 2014, 57, 5845. doi: 10.1021/jm4017625
[38]	Lovering, F.; Bikker, J.; Humblet, C. J. Med. Chem. 2009, 52, 6752. doi: 10.1021/jm901241e pmid: 19827778
[39]	Murahashi, S.-I.; Hirano, T.; Yano, T. J. Am. Chem. Soc. 1978, 100, 348. doi: 10.1021/ja00469a093
[40]	(a) Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681. doi: 10.1021/cr900202j pmid: 19938813
	(b) Guillena, G.; Ramln, D. J.; Yus, M. Chem. Rev. 2010, 110, 1611. doi: 10.1021/cr9002159 pmid: 19938813
	(c) Corma, A.; Navas, J.; Sabater, M. J. Chem. Rev. 2018, 118, 1410. doi: 10.1021/acs.chemrev.7b00340 pmid: 19938813
[41]	(a) Khai, B.-T.; Concilio, C.; Porzi, G. J. Organomet. Chem. 1981, 208, 249. doi: 10.1016/S0022-328X(00)82680-7
	(b) Khai, B.-T.; Concilio, C.; Porzi, G. J. Org. Chem. 1981, 46, 1759. doi: 10.1021/jo00321a056
[42]	(a) Hollmann, D.; B-hn, S.; Tillack, A.; Beller, M. Angew. Chem. Int. Ed. 2007, 46, 8291. pmid: 17890660
	(b) Saidi, O.; Blacker, A. J.; Farah, M. M.; Marsden, S. P.; Williams, J. M. J. Angew. Chem. Int. Ed. 2009, 48, 7375. doi: 10.1002/anie.200904028 pmid: 17890660
	(c) Wang, D.; Zhao, K.; Xu, C.; Miao, H.; Ding, Y. ACS Catal. 2014, 4, 3910. doi: 10.1021/cs5009909 pmid: 17890660
[43]	Yin, Z.; Zeng, H.; Wu, J.; Zheng, S.; Zhang, G. ACS Catal. 2016, 6, 6546. doi: 10.1021/acscatal.6b02218
[44]	(a) Xie, Y.; Hu, J.; Wang, Y.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613. doi: 10.1021/ja310848x
	(b) Xie, Y.; Hu, J.; Xie, P.; Qian, B.; Huang, H. J. Am. Chem. Soc. 2013, 135, 18327. doi: 10.1021/ja410611b
	(c) Hu, J.; Xie, Y.; Huang, H. Angew. Chem. Int. Ed. 2014, 53, 7272. doi: 10.1002/anie.201403774
	(d) Qin, G.; Li, L.; Li, J.; Huang, H. J. Am. Chem. Soc. 2015, 137, 12490. doi: 10.1021/jacs.5b08476
	(e) Liu, Y.; Xie, Y.; Wang, H.; Huang, H. J. Am. Chem. Soc. 2016, 138, 4314. doi: 10.1021/jacs.6b00976
	(f) Qi, X.; Liu, S.; Lan, Y. Organometallic 2016, 35, 1582. doi: 10.1021/acs.organomet.6b00234
[45]	Yu, B.; Zou, S.; Liu, H.; Huang, H. J. Am. Chem. Soc. 2020, 142, 18341. doi: 10.1021/jacs.0c10615

碳-杂原子键复分解反应的研究进展