Recent Advance of Transition Metal-Free Catalyzed Suzuki-Type Cross Coupling Reaction

doi:10.6023/cjoc202208008

Abstract

Transition metal catalyzed Suzuki coupling reaction serves as one of the most versatile and widespread methods for the C-C bonds formation, which greatly promotes the development of synthetic chemistry. Currently, the Suzuki coupling reactions heavily rely on noble palladium-catalyzed system. However, the high cost, toxicity and low reserves of palladium have become the main obstacles for their development in organic synthesis. Over the past two decades, metal-free catalyzed Suzuki-Type cross coupling reactions earned extensive concern, and a large number of efficient and new reaction systems have been reported. In this review, the recent progresses of metal-free catalyzed Suzuki-Type cross coupling reactions are summarized, mainly including bases, organometallic reagents and organic molecules promoted reactions. In addition, the mechanism of reaction is also discussed in this review.

Key words: metal-free catalysis, Suzuki cross-coupling, organic synthesis, base promoting, coupling reaction

Cite this article

Biao Ma, Miaomiao Zhang, Zhanyu Li, Jinsong Peng, Chunxia Chen. Recent Advance of Transition Metal-Free Catalyzed Suzuki-Type Cross Coupling Reaction[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 455-470.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 36

Scheme 1. Suzuki-Type cross coupling reaction of allyl bromides with aryl boroic acids

Scheme 2. Suzuki-Type cross coupling reaction of sulfonate with aryl boroic acids

Scheme 3. Possible mechanism for coupling sulfonate with boroic acids

Scheme 4. Suzuki-Type cross coupling reaction between allyl bromines and aryl boroic acids

Scheme 5. Suzuki-Type cross coupling reaction between propargyl bromines and aryl boric acids

Scheme 6. Two types of coupling reactions

Scheme 7. Suzuki-Type cross coupling reaction of benzyl halides and aryl boroic acids

Scheme 8. Possible mechanism for coupling benzyl halides and aryl boroic acids

Scheme 9. Suzuki-Type cross coupling reaction of alkyl halides or pseudohalides with alkenyl boric acids

Scheme 10. Mechanistic verification experiments related to the coupling of alkyl halides or pseudohalides with alkenyl boric acids

Scheme 11. Suzuki-Type cross coupling reaction coupling of alkenyl boronic acids with sp3 electrophiles

Scheme 12. Possible mechanism for coupling alkenyl boronic acids with sp3 electrophiles

Scheme 13. Suzuki-Type cross coupling reaction of benzyl halides with aryl boronic acids

Scheme 14. Possible mechanism for coupling benzyl halides with aryl boronic acids

Scheme 15. Suzuki-Type cross coupling reaction of benzoyl chlorides and aryl boronic acids

Scheme 16. Suzuki-Type cross coupling reaction of deborylatives with halogenated hydrocarbons

Scheme 17. Mechanistic verification experiments related to the coupling of deborylatives with halogenated hydrocarbons

Scheme 18. Suzuki-Type cross coupling reaction of tert-benzyl borate esters with electrophilic reagents

Scheme 19. Mechanistic verification experiments related to the coupling of tert-benzyl boronic acid esters with electrophilic reagents

Scheme 20. Possible mechanism for coupling tert-benzyl boronic acid esters with electrophilic reagents

Scheme 21. Suzuki-Type cross coupling reaction of electron-rich aromatics with borate esters

Scheme 22. Possible mechanism for coupling electron-rich aromatics with borate esters

Scheme 23. Effect of the purity of arylboronic acid on the reaction

Scheme 24. Elucidation of the species generated upon mixing an arylboronic acid and diethylzinc

Scheme 25. Suzuki-Type cross coupling reaction between aryl boric anhydrides and iodobenzenes

Scheme 26. Possible mechanism for coupling arylboronic anhydride with iodobenzene

Scheme 27. Stereospecific mono- and difluoromethylation of boronic esters

Scheme 28. Suzuki-Type cross coupling reaction of benzyl halides with aryl boronic acids

Scheme 29. Possible mechanism for coupling benzyl halides with aryl boronic acids

Scheme 30. Deactivation of organic small molecule sulfur catalysts

Scheme 31. Suzuki-Type cross coupling reaction catalyzed by organic small molecule sulfur

Scheme 32. Suzuki-Type cross coupling reaction between aryl boronic acids and aryl halides

Scheme 33. Possible mechanism of Suzuki-Type coupling facilitated by small molecule sulfur

Scheme 34. Suzuki-Type cross coupling reaction catalyzed by organophosphorus

Scheme 35. Light-induced Suzuki-Type cross-coupling reaction

Scheme 36. Possible mechanism of light-induced Suzuki-Type coupling

References 37

[1]	(a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. doi: 10.1021/cr00039a007
	(b) Patel, K. N.; Bedekar. A. V. Catal. Lett. 2015, 145, 1710 doi: 10.1007/s10562-015-1570-z
	(c) Zhang, L.; Yang, C.; Guo, X.-F.; Mo, F.-Y. Chin. J. Org. Chem. 2021, 41, 3492. (in Chinese) doi: 10.6023/cjoc202103040
	(张雷, 杨晨, 郭雪峰, 莫凡洋, 有机化学, 2021, 41, 3492.) doi: 10.6023/cjoc202103040
[2]	Schneider, N.; Lowe, D. M.; Sayle, R, A.; Tarselli, M.; Landrum, G. J. Med. Chem. 2016, 59, 4385. doi: 10.1021/acs.jmedchem.6b00153 pmid: 27028220
[3]	Li, Y.; Duan, G. T.; Liu, G. Q.; Cai, W. P. Chem. Soc. Rev. 2013, 42, 3614. doi: 10.1039/c3cs35482b
[4]	Adamo, C.; Amatore, C.; Ciofini, I.; Jutand, A.; Lakmini, H. J. Am. Chem. Soc. 2006, 128, 6829. doi: 10.1021/ja0569959
[5]	(a) Narayan, S.; Muldoon, J.; Finn, M.; Fokin, V.; Kolb, H.; Sharpless, K. J. Angew. Chem. Int. Ed. 2005, 44, 21. doi: 10.1002/ange.19310440105
	(b) Kambe, N.; Iwasaki, T.; Terao, J. Chem. Soc. Rev. 2011, 40, 4937 doi: 10.1039/c1cs15129k
	(c) Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299. doi: 10.1038/nature13274
[6]	Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417. doi: 10.1021/cr100327p
[7]	Felpin, F. X.; Ayad, T.; Mitra, S. Eur. J. Org. Chem. 2006, 2679.
[8]	(a) Bedford, R. B.; Brenner, P. B.; Carter, E.; Carvell, T. W; Cogswell, P. M.; Gallagher, T.; Harvey, J. N.; Murphy, D. M.; Neeve, E. C.; Nunn, J.; Pye, D. M. Chem.-Eur. J. 2014, 20, 7935. doi: 10.1002/chem.201402174 pmid: 22148416
	(b) Hashimoto, T.; Hatakeyama, T.; Nakamura, M. J. Org. Chem. 2012, 77, 1168 doi: 10.1021/jo202151f pmid: 22148416
	(c) Hatakeyama, T.; Hashimoto, T.; Kathriarachchi, K. K. A. D. S.; Zenmyo, T.; Seike, H.; Nakamura, M. Angew. Chem. 2012, 124, 8964. doi: 10.1002/ange.201202797 pmid: 22148416
[9]	Neely, J. A.; Bezdek, M. J.; Chirik, P. J. ACS Cent. Sci. 2016, 2, 12. doi: 10.1021/acscentsci.6b00002
[10]	(a) Shields, J. D.; Gray, E. E.; Doyle, A. G. Org. Lett. 2015, 17, 2166. doi: 10.1021/acs.orglett.5b00766 pmid: 25886092
	(b) Mastalir, M.; Stöger, B.; Pittenauer, E.; Allmaier, G.; Kirchner, K. Org. Lett. 2016, 18, 3186 doi: 10.1021/acs.orglett.6b01398 pmid: 25886092
	(c) Shi, S.; Meng, G.; Szostak, M. Angew. Chem., Int. Ed. 2016, 55, 6959. doi: 10.1002/anie.201601914 pmid: 25886092
	(d) Shi, S.; Meng, G.; Szostak, M. Angew. Chem., Int. Ed. 2016, 55, 6959. doi: 10.1002/anie.201601914 pmid: 25886092
	(e) Chen, G.-J.; Du, J.-S. Chin. J. Org. Chem. 2014, 34, 65. (in Chinese) doi: 10.6023/cjoc201307035 pmid: 25886092
	(陈国军, 杜建时, 有机化学, 2014, 34, 65.) doi: 10.6023/cjoc201307035 pmid: 25886092
	(f) Li, Y.-Q.; Fan, Y.-H.; Jia, Q.-F. Chin. J. Org. Chem. 2019, 39, 350. (in Chinese) doi: 10.6023/cjoc201806038 pmid: 25886092
	(李娅琼, 范玉航, 贾乾发, 有机化学, 2019, 39, 350.) doi: 10.6023/cjoc201806038 pmid: 25886092
[11]	(a) Basnet, P.; Thapa, S.; Dickie, D. A.; Giri, R. Chem. commun. 2016, 52, 11072. doi: 10.1039/C6CC05114F
	(b) Sun, Y.; Yi, J.; Lu, X.; Zhang, Z.; Xiao, B.; Fu, Y. Chem. Commun. 2014, 50, 11060 doi: 10.1039/C4CC05376A
	(c) Zhou, Y. Q.; You, W.; Smith, K. B.; Brown, K. M. Angew. Chem. 2014, 126, 3543. doi: 10.1002/ange.201310275
[12]	Leadbeater, N. E.; Marco, M. Angew. Chem. 2003, 115, 11512.
[13]	Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. D. J. Org. Chem. 2005, 70, 161. pmid: 15624918
[14]	Scrivanti, A.; Beghetto, V.; Bertoldini, M.; Matteoli U. Eur. J. Org. Chem. 2012, 264.
[15]	Tian, D. S.; Li, C. X.; Gu, G. X.; Peng, H.; Zhang, X.; Tang, W. J. Angew. Chem., Int. Ed. 2018, 57, 7176. doi: 10.1002/anie.201712829
[16]	Urbani, P.; Cascio, M. G.; Ramunno, A.; Bisogno, T.; Saturninno, C.; Marzo, V. D. Bioorg. Med. Chem. 2008, 16, 7510. doi: 10.1016/j.bmc.2008.06.001
[17]	Ueda, M.; Nishimura, K.; Kashima, R.; Ryu, I. Synlett 2012, 23, 1089.
[18]	(a) Huang, X. T.; Chen, Q. Y. J. Org. Chem. 2001, 66, 4651. pmid: 11421787
	(b) Loy, R. N.; Sanford, M. S. Org. Lett. 2011, 13, 2548. doi: 10.1021/ol200628n pmid: 11421787
[19]	Ueda, M.; Nishimura, K.; Ryu, I. Synlett 2013, 24, 1683. doi: 10.1055/s-0033-1339199
[20]	(a) Yoshida, M.; Gotou, T.; Ihara, M. Tetrahedron Lett. 2004, 45, 5573. doi: 10.1016/j.tetlet.2004.05.147 pmid: 16468806
	(b) Moriya, T.; Miyaura, N.; Suzuki, A. Synlett 1994, 149. pmid: 16468806
	(c) Yoshida, M.; Ueda, H.; Ihara, M. Tetrahedron Lett. 2005, 46, 6705. pmid: 16468806
	(d) Molander, G. A.; Sommers, E. M.; Neufeldt, S. R. J. Org. Chem. 2006, 71, 1563. doi: 10.1021/jo052201x pmid: 16468806
[21]	Ueda, M.; Nakakoji, D.; Kuwahara, Y.; Nishimura, K.; Ryu, I. Tetrahedron Lett. 2016, 57, 4142. doi: 10.1016/j.tetlet.2016.07.089
[22]	Li, C. X; Zhang, Y. Y.; Sun, Q.; Gu, T.; Peng, H.; Tang, W. J. J. Am. Chem. Soc. 2016, 138, 10774. doi: 10.1021/jacs.6b06285
[23]	Liu, S. W.; Zeng, X. J.; Hammond, G. B.; Xu, B. Adv. Synth. Catal. 2018, 360, 3667. doi: 10.1002/adsc.201800826
[24]	Wu, G. J.; Xu, S.; Deng, Y. F.; Wu, C. Q.; Zhao, X.; Ji, W. Z.; Zhang, Y.; Wang, J. B. Tetrahedron 2016, 72, 8022. doi: 10.1016/j.tet.2016.10.031
[25]	(a) Urawa, Y.; Ogura, K. Tetrahedron Lett. 2003, 44, 271. doi: 10.1016/S0040-4039(02)02501-7 pmid: 19548645
	(b) Baughman, B. M.; Stennett, E.; Lipner, R. F.; Rudawsky, A. C.; Schmidtke, S. J. Phys. Chem. A 2009, 113, 8011. doi: 10.1021/jp810256x pmid: 19548645
[26]	(a) Furstner, A.; Voigtlander, D.; Schrader, W.; Giebel, D.; Reetz, M. T. Org. Lett. 2001, 3, 417. doi: 10.1021/ol0069251
	(b) Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H. Chem. Commun. 2000, 1695.
[27]	Jadhav, S.; Rashinkar, G.; Salunkhe, R.; Kumbhar, A. Tetrahedron Lett. 2017, 58, 3201. doi: 10.1016/j.tetlet.2017.06.048
[28]	Hong, K.; Liu, X.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 10581. doi: 10.1021/ja505455z pmid: 25019925
[29]	Takeda, M.; Nagao, K.; Ohmiya, H. Angew. Chem., Int. Ed. 2020, 59, 22460. doi: 10.1002/anie.202010251
[30]	Bonet, A.; Odachowski, M.; Leonori, D.; Essafi, S.; Aggarwal, V. K. Nat. Chem. 2014, 6, 584. doi: 10.1038/nchem.1971
[31]	Okura, K.; Teranishi, T.; Yoshida, Y.; Shirakawa, E. Angew. Chem., Int. Ed. 2018, 57, 7186. doi: 10.1002/anie.201802813
[32]	Fasano, V.; Winter, N.; Noble, A.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2020, 59, 8502. doi: 10.1002/anie.202002246
[33]	He, Z. Q.; Song, F. F.; Sun, H.; Huang, Y. J. Am. Chem. Soc. 2018, 140, 2693. doi: 10.1021/jacs.8b00380
[34]	Xu, J. W.; He, Z. Q.; Zhang, J. W.; Chen, J.; Huang, Y. Angew. Chem., Int. Ed. 2022, 61, e202211408.
[35]	Choghamarani, A.; Taherinia, Z. ChemistrySelect 2019, 4, 4735. doi: 10.1002/slct.201900801
[36]	Tian, W. F.; He, K. H.; Li, N.; Fen.; Liu.; Mai, X.; Feng, L. H.; He, Y. Q. ChemistrySelect 2020, 5, 4496. doi: 10.1002/slct.202000416
[37]	Liu, W. B; Li, J. B.; Querard, P.; Li, C. J. J. Am. Chem. Soc. 2019, 141, 6755. doi: 10.1021/jacs.9b02684

无过渡金属催化的Suzuki-Type交叉偶联反应研究进展