Organic Letters
ORCID
Letter
(10) (a) Meng, G.; Shi, S.; Szostak, M. ACS Catal. 2016, 6, 7335.
(b) Shi, S.; Szostak, M. Org. Lett. 2016, 18, 5872. (c) Meng, G.; Szostak,
M. ACS Catal. 2017, 7, 7251.
(11) (a) Larock, R. C. Comprehensive Organic Transformations; Wiley:
New York, 1999. (b) Zabicky, J. The Chemistry of Amides; Interscience:
New York, 1970. (c) See ref 6.
(12) (a) Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451.
(b) Pattabiraman, V. R.; Bode, J. W. Nature 2011, 480, 471. (c) Kaspar,
A. A.; Reichert, J. M. Drug Discovery Today 2013, 18, 807.
(13) Davidsen, S. K.; May, P. D.; Summers, J. B. J. Org. Chem. 1991, 56,
5482.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
(14) Mahatthananchai, J.; Dumas, A.; Bode, J. W. Angew. Chem., Int. Ed.
2012, 51, 10954.
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Rutgers University and the NSF (CAREER CHE-1650766) are
gratefully acknowledged for support. The Bruker 500 MHz
spectrometer was supported by the NSF-MRI grant (CHE-
1229030). P.L. thanks the China Scholarship Council for a
fellowship (No. 201606350069). S.P.N. thanks the ERC (Adv.
Researcher Grant 227817) for support.
(15) (a) Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.;
Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101. (b) Navarro, O.; Marion,
N.; Mei, J.; Nolan, S. P. Chem. - Eur. J. 2006, 12, 5142. (c) Marion, N.;
Nolan, S. P. Acc. Chem. Res. 2008, 41, 1440. (d) Rivas-Nass, A.; Winde,
R.; Briel, O.; Le Ret, C.; Karch, R. Chim. Oggi 2007, 25, 15.
(16) Palladium-Catalyzed Coupling Reactions: Practical Aspects and
Future Developments; Molnar, A., Ed.; Wiley: Weinheim, 2013.
(17) For select applications of biaryl ketones, see: (a) Jabeen, I.;
Pleban, K.; Rinner, U.; Chiba, P.; Ecker, G. F. J. Med. Chem. 2012, 55,
3261. (b) Sharmoukh, W.; Ko, K. C.; Noh, C.; Lee, J. Y.; Son, S. U. J. Org.
Chem. 2010, 75, 6708. (c) Kameswaran, V. WO2001051440 A1, Jul 19,
2001. (d) Leze, M. P.; Le Borgne, M.; Pinson, P.; Palusczak, A.; Duflos,
M.; Le Baut, G.; Hartmann, R. W. Bioorg. Med. Chem. Lett. 2006, 16,
1134.
REFERENCES
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(1) (a) Takise, R.; Muto, K.; Yamaguchi, J. Chem. Soc. Rev. 2017, 46,
5864. (b) Meng, G.; Shi, S.; Szostak, M. Synlett 2016, 27, 2530. (c) Liu,
C.; Szostak, M. Chem. - Eur. J. 2017, 23, 7157. (d) Dander, J. E.; Garg, N.
K. ACS Catal. 2017, 7, 1413.
(2) (a) Metal-Catalyzed Cross-Coupling Reactions and More; de Meijere,
A., Brase, S., Oestreich, M., Eds.; Wiley: New York, 2014. (b) Science of
Synthesis: Cross-Coupling and Heck-Type Reactions; Molander, G. A.,
Wolfe, J. P., Larhed, M., Eds.; Thieme: Stuttgart, 2013.
(18) For reviews on NHC ligands, see: (a) Science of Synthesis: N-
Heterocyclic Carbenes in Catalytic Organic Synthesis, Nolan, S. P., Cazin,
C. S. J., Eds.; Thieme: Stuttgart, 2017. (b) Fortman, G. C.; Nolan, S. P.
Chem. Soc. Rev. 2011, 40, 5151. (c) N-Heterocyclic Carbenes; Nolan, S. P.,
Ed.; Wiley: Weinheim, 2014. (d) N-Heterocyclic Carbenes in Transition
Metal Catalysis; Cazin, C. S. J., Ed.; Springer: New York, 2011.
(e) Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Nature
2014, 510, 485. (f) Valente, C.; Calimsiz, S.; Hoi, K. H.; Mallik, D.;
Sayah, M.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 3314.
(19) For reviews on stereoelectronic properties of NHCs, see:
(a) Nelson, D. J.; Nolan, S. P. Chem. Soc. Rev. 2013, 42, 6723.
(b) Clavier, H.; Nolan, S. P. Chem. Commun. 2010, 46, 841. (c) Diez-
Gonzalez, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874.
(20) For select examples of NHC ligands in amide cross-coupling, see:
(a) Weires, N. A.; Baker, E. L.; Garg, N. K. Nat. Chem. 2015, 8, 75.
(b) Simmons, B. J.; Weires, N. A.; Dander, J. E.; Garg, N. K. ACS Catal.
2016, 6, 3176. (c) Baker, E. L.; Yamano, M. M.; Zhou, Y.; Anthony, S.
M.; Garg, N. K. Nat. Commun. 2016, 7, 11554. (d) Medina, J. M.;
Moreno, J.; Racine, S.; Du, S.; Garg, N. K. Angew. Chem., Int. Ed. 2017,
56, 6567. (e) Dander, J. E.; Baker, E. L.; Garg, N. K. Chem. Sci. 2017, 8,
6433. (f) Lei, P.; Meng, G.; Ling, Y.; An, J.; Szostak, M. J. Org. Chem.
2017, 82, 6638. (g) Shi, S.; Szostak, M. Chem. Commun. 2017, 53, 10584.
(h) See refs 3g and 5.
(21) Reviews on well-defined Pd catalysts: (a) Hazari, N.; Melvin, P.
R.; Beromi, M. M. Nat. Rev. Chem. 2017, 1, 25. (b) Li, H.; Johansson-
Seechurn, C. C. C.; Colacot, T. J. ACS Catal. 2012, 2, 1147.
(22) For a review on sterically demanding NHCs, see: Izquierdo, F.;
Manzini, S.; Nolan, S. P. Chem. Commun. 2014, 50, 14926.
(23) Joshi-Pangu, A.; Wang, C. Y.; Biscoe, M. J. Am. Chem. Soc. 2011,
133, 8478.
(24) Melvin, P. R.; Nova, A.; Balcells, D.; Dai, W.; Hazari, N.;
Hruszkewycz, D. P.; Shah, H. P.; Tudge, M. T. ACS Catal. 2015, 5, 3680.
̈
(3) For representative acyl coupling, see: (a) Hie, L.; Nathel, N. F. F.;
Shah, T. K.; Baker, E. L.; Hong, X.; Yang, Y. F.; Liu, P.; Houk, K. N.;
Garg, N. K. Nature 2015, 524, 79. (b) Meng, G.; Szostak, M. Org. Lett.
2015, 17, 4364. (c) Lei, P.; Meng, G.; Szostak, M. ACS Catal. 2017, 7,
1960. (d) Meng, G.; Lei, P.; Szostak, M. Org. Lett. 2017, 19, 2158.
(e) Amani, J.; Alam, R.; Badir, S.; Molander, G. A. Org. Lett. 2017, 19,
2426. (f) Ni, S.; Zhang, W.; Mei, H.; Han, J.; Pan, Y. Org. Lett. 2017, 19,
2536. (g) Lei, P.; Meng, G.; Shi, S.; Ling, Y.; An, J.; Szostak, R.; Szostak,
M. Chem. Sci. 2017, 8, 6525 and references cited therein.
(4) For representative decarbonylative coupling, see: (a) Meng, G.;
Szostak, M. Angew. Chem., Int. Ed. 2015, 54, 14518. (b) Shi, S.; Meng, G.;
Szostak, M. Angew. Chem., Int. Ed. 2016, 55, 6959. (c) Meng, G.; Szostak,
M. Org. Lett. 2016, 18, 796. (d) Dey, A.; Sasmal, S.; Seth, K.; Lahiri, G.
K.; Maiti, D. ACS Catal. 2017, 7, 433. (e) Yue, H.; Guo, L.; Liao, H. H.;
Cai, Y.; Zhu, C.; Rueping, M. Angew. Chem., Int. Ed. 2017, 56, 4282.
(f) Yue, H.; Guo, L.; Lee, S. C.; Liu, X.; Rueping, M. Angew. Chem., Int.
Ed. 2017, 56, 3972. (g) Shi, S.; Szostak, M. Org. Lett. 2017, 19, 3095 and
references cited therein.
(5) For representative tandem coupling, see: Walker, J. A.; Vickerman,
K. L.; Humke, J. N.; Stanley, L. M. J. Am. Chem. Soc. 2017, 139, 10228
and references cited therein.
(6) Greenberg, A.; Breneman, C. M.; Liebman, J. F., Eds. The Amide
Linkage: Structural Significance in Chemistry, Biochemistry, and Materials
Science; Wiley: New York, 2000.
(7) Review on electrophilic activation of amides: (a) Kaiser, D.;
Maulide, N. J. Org. Chem. 2016, 81, 4421. For an overview of amide
cross-coupling, see: (b) Ruider, S. A.; Maulide, N. Angew. Chem., Int. Ed.
2015, 54, 13856. For a report on using amides as latent substrates, see:
(c) Valerio, V.; Petkova, D.; Madelaine, C.; Maulide, N. Chem. - Eur. J.
2013, 19, 2606.
(8) (a) Szostak, R.; Shi, S.; Meng, G.; Lalancette, R.; Szostak, M. J. Org.
Chem. 2016, 81, 8091. (b) Pace, V.; Holzer, W.; Meng, G.; Shi, S.;
Lalancette, R.; Szostak, R.; Szostak, M. Chem. - Eur. J. 2016, 22, 14494.
(c) Szostak, R.; Meng, G.; Szostak, M. J. Org. Chem. 2017, 82, 6373 and
references cited therein. (d) See ref 1c.
(26) Christmann, U.; Vilar, R. Angew. Chem., Int. Ed. 2005, 44, 366.
(27) Zinser, C. M.; Nahra, F.; Brill, M.; Meadows, R. E.; Cordes, D. B.;
Slawin, A. M. Z.; Nolan, S. P.; Cazin, C. S. J. Chem. Commun. 2017, 53,
7990.
(9) Review on acyl-metal intermediates: (a) Dzik, W. I.; Lange, P. P.;
Gooßen, L. J. Chem. Sci. 2012, 3, 2671. For the seminal study on cross-
coupling of unactivated aryl esters, see: (b) Amaike, K.; Muto, K.;
Yamaguchi, J.; Itami, K. J. Am. Chem. Soc. 2012, 134, 13573.
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