Nickel-catalysed Suzuki–Miyaura coupling of amides (2024)

1. Muci, A. R. & Buchwald, S. L. in Cross-Coupling Reactions: A Practical Guide (ed. Miyaura, N.) 131–209 (Topics in Current Chemistry 219, Springer, 2002).
   https://doi.org/10.1007/3-540-45313-X_5
2. Tasker, S. Z., Standley, E. A. & Jamison, T. F. Recent advances in hom*ogeneous nickel catalysis. Nature 509, 299–309 (2014).
   https://doi.org/10.1038/nature13274
3. Mesganaw, T. & Garg, N. K. Ni- and Fe-catalyzed cross-coupling reactions of phenol derivatives. Org. Process. Res. Dev. 17, 29–39 (2013).
   https://doi.org/10.1021/op300236f
4. Rosen, B. M. et al. Nickel-catalyzed cross-couplings involving carbon–oxygen bonds. Chem. Rev. 111, 1346–1416 (2011).
   https://doi.org/10.1021/cr100259t
5. Blakey, S. B. & MacMillan, D. W. C. The first Suzuki cross-couplings of aryltrimethylammonium salts. J. Am. Chem. Soc. 125, 6046–6047 (2003).
   https://doi.org/10.1021/ja034908b
6. Zhang, X.-Q. & Wang, Z.-X. Nickel-catalyzed cross-coupling of aryltrimethylammonium triflates and amines. Org. Biomol. Chem. 12, 1448–1453 (2014).
   https://doi.org/10.1039/c3ob41989d
7. Tobisu, M., Nakamura, K. & Chatani, N. Nickel-catalyzed reductive and borylative cleavage of aromatic carbon–nitrogen bonds in N-aryl amides and carbamates. J. Am. Chem. Soc. 136, 5587–5590 (2014).
   https://doi.org/10.1021/ja501649a
8. Hie, L. et al. Conversion of amides to esters by the nickel-catalyzed activation of amide C–N bonds. Nature 524, 79–83 (2015).
   https://doi.org/10.1038/nature14615
9. Louie, J. in N-Heterocyclic Carbenes in Synthesis (ed. Nolan, S. P.) 163–182 (Wiley, 2006).
   https://doi.org/10.1002/9783527609451.ch7
10. Hoshimoto, Y., Hayashi, Y., Suzuki, H., Ohashi, M. & Ogoshi, S. One-pot, single-step, and gram-scale synthesis of mononuclear [(η6-arene)Ni(N-heterocyclic carbene)] complexes: useful precursors of the Ni0-NHC unit. Organometallics 33, 1276–1282 (2014).
    https://doi.org/10.1021/om500088p
11. Greenberg, A., Breneman, C. M. & Liebman, J. F. The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science (Wiley, 2002).
12. Blangetti, M., Rosso, H., Prandi, C., Deagostino, A. & Venturello, P. Suzuki–Miyaura cross-coupling in acylation reactions, scope and recent developments. Molecules 18, 1188–1213 (2013).
    https://doi.org/10.3390/molecules18011188
13. Chen, Q., Fan, X.-H., Zhang, L.-P. & Yang, L.-M. Nickel-catalyzed cross-coupling of carboxylic anhydrides with arylboronic acids. RSC Adv. 4, 53885–53890 (2014).
    https://doi.org/10.1039/C4RA11520A
14. Li, X. & Zou, G. Acylative Suzuki coupling of amides: acyl-nitrogen activation via synergy of independently modifiable activating groups. Chem. Commun. 51, 5089–5092 (2015).
    https://doi.org/10.1039/C5CC00430F
15. Meng, G. & Szostak, M. Sterically controlled Pd-catalyzed chemoselective ketone synthesis via N–C cleavage in twisted amides. Org. Lett. 17, 4364–4367 (2015).
    https://doi.org/10.1021/acs.orglett.5b02209
16. Nahm, S. & Weinreb, S. M. N-Methoxy-N-methylamides as effective acylating agents. Tetrahedron Lett. 22, 3815–3818 (1981).
    https://doi.org/10.1016/S0040-4039(01)91316-4
17. Balasubramaniam, S. & Aidhen, I. S. The growing synthetic utility of the Weinreb amide. Synthesis 3707–3738 (2008).
    https://doi.org/10.1055/s-0028-1083226
18. Lennox, J. J. A. & Lloyd-Jones, G. C. Selection of boron reagents for Suzuki–Miyaura coupling. Chem. Soc. Rev. 43, 412–443 (2014).
    https://doi.org/10.1039/C3CS60197H
19. Miyaura, N. & Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 95, 2457–2483 (1995).
    https://doi.org/10.1021/cr00039a007
20. Quasdorf, K. W. et al. Suzuki–Miyaura cross-coupling of aryl carbamates and sulfamates: experimental and computational studies. J. Am. Chem. Soc. 133, 6352–6363 (2011).
    https://doi.org/10.1021/ja200398c
21. Guan, B.-T., Wang, Y., Li, B.-J., Yu, D.-G. & Shi, Z.-J. Biaryl construction via Ni-catalyzed C–O activation of phenolic carboxylates. J. Am. Chem. Soc. 130, 14468–14470 (2008).
    https://doi.org/10.1021/ja8056503
22. Antoft-Finch, A., Blackburn, T. & Snieckus, V. N,N-Diethyl O-carbamate: directed metalation group and orthogonal Suzuki–Miyaura cross-partner. J. Am. Chem. Soc. 131, 17750–17752 (2009).
    https://doi.org/10.1021/ja907700e
23. Jezorek, R. L. et al. Coupling of aryl sulfamates with aryl neopentylglycolboronates at room temperature. Org. Lett. 16, 6326–6329 (2014).
    https://doi.org/10.1021/ol503061c
24. Yamamoto, T., Ishizu, J., Kohara, T., Komiya, S. & Yamamoto, A. Oxidative addition of aryl carboxylates to nickel(0) complexes involving cleavage of the acyl–oxygen bond. J. Am. Chem. Soc. 102, 3758–3764 (1980).
    https://doi.org/10.1021/ja00531a016
25. Amaike, K., Muto, K., Yamaguchi, J. & Itami, K. Decarbonylative C–H coupling of azoles and aryl esters: unprecedented nickel catalysis and application to the synthesis of muscoride A. J. Am. Chem. Soc. 134, 13573–13576 (2012).
    https://doi.org/10.1021/ja306062c
26. Muto, K., Yamaguchi, J., Musaev, D. G. & Itami, K. Decarbonylative organoboron cross-coupling of esters by nickel catalysis. Nature Commun. 6, 7508 (2015).
    https://doi.org/10.1038/ncomms8508
27. Vitaku, E., Smith, D. T. & Njardarson, J. T. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals. J. Med. Chem. 57, 10257–10274 (2014).
    https://doi.org/10.1021/jm501100b
28. DrugBank Version 4.3 (Wishart Research Group, Alberta).
29. Hu, L. et al. Novel potent antimitotic heterocyclic ketones: synthesis, antiproliferative activity, and structure–activity relationships. Bioorg. Med. Chem. Lett. 17, 3613–3617 (2007).
    https://doi.org/10.1016/j.bmcl.2007.04.048
30. Billingsley, K. & Buchwald, S. L. Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki–Miyaura reaction of heteroaryl halides and heteroaryl boronic acid and esters. J. Am. Chem. Soc. 129, 3358–3366 (2007).
    https://doi.org/10.1021/ja068577p

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