G
Synthesis
S. Shi, M. Szostak
Special Topic
2
017, 7, 1960. (f) Liu, C.; Liu, Y.; Liu, R.; Lalancette, R.; Szostak,
79, 4253. (e) Haag, B.; Mosrin, M.; Ila, H.; Malakhov, V.; Knochel,
P. Angew. Chem. Int. Ed. 2011, 50, 9794. Selected recent exam-
ples: (f) Thapa, S.; Kafle, A.; Gurung, S. K.; Montoya, A.; Riedl, P.;
Giri, R. Angew. Chem. Int. Ed. 2015, 54, 8236. (g) Joshi-Pangu, A.;
Ganesh, M.; Biscoe, M. R. Org. Lett. 2011, 13, 1218. (h) Xie, L. G.;
Wang, Z. X. Angew. Chem. Int. Ed. 2011, 50, 4901. (i) Thaler, T.;
Haag, B.; Gavryushin, A.; Schober, K.; Hartmann, E.; Gschwind,
R. M.; Zipse, H.; Mayer, P.; Knochel, P. Nat. Chem. 2010, 2, 125.
Negishi coupling of cyclic anhydrides: (j) Bercot, E. A.; Rovis, T.
J. Am. Chem. Soc. 2002, 124, 174. (k) Johnson, J. B.; Rovis, T. Acc.
Chem. Res. 2008, 41, 327. Fukuyama coupling: (l) Tokuyama, H.;
Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett.
1998, 39, 3189. (m) Kunchithapatham, K.; Eichman, C. E.;
Stambuli, J. P. Chem. Commun. 2011, 47, 12697. (n) Oost, R.;
Misale, A.; Maulide, N. Angew. Chem. Int. Ed. 2016, 55, 4587.
(o) Misale, A.; Niyomchon, S.; Luparia, M.; Maulide, N. Angew.
Chem. Int. Ed. 2014, 53, 7068.
R.; Szostak, M. Org. Lett. 2017, 19, 1434. (g) Meng, G.; Lei, P.;
Szostak, M. Org. Lett. 2017, 19, 2158.
(
7) The first example of C–C bond formation by amide bond cross-
coupling was reported by the Zou group: Li, X.; Zou, G. Chem.
Commun. 2015, 51, 5089.
(
8) (a) Hu, J.; Zhao, Y.; Liu, J.; Zhang, Y.; Shi, Z. Angew. Chem. Int. Ed.
2016, 55, 8718. (b) Cui, M.; Wu, H.; Jian, J.; Wang, H.; Liu, C.;
Daniel, S.; Zeng, Z. Chem. Commun. 2016, 52, 12076. (c) Wu, H.;
Cui, M.; Jian, J.; Zheng, Z. Adv. Synth. Catal. 2016, 358, 3876.
(d) Wu, H.; Liu, T.; Cui, M.; Li, Y.; Jian, J.; Wang, H.; Zeng, Z. Org.
Biomol. Chem. 2017, 15, 536. (e) Dey, A.; Sasmai, S.; Seth, K.;
Lahiri, G. K.; Maiti, D. ACS Catal. 2017, 7, 433. (f) Liu, L.; Chen, P.;
Sun, Y.; Wu, Y.; Chen, S.; Zhu, J.; Zhao, Y. J. Org. Chem. 2016, 81,
11686. For a recent excellent use of N-glutarimides in decarbon-
ylative N–C coupling, see: (g) Yue, H.; Guo, L.; Liao, H. H.; Cai, Y.;
Zhu, C.; Rueping, M. Angew. Chem. Int. Ed. 2017, 56, 4282.
(
h) Yue, H.; Guo, L.; Lee, S. C.; Liu, X.; Rueping, M. Angew. Chem.
(16) Reviews on Ni-catalysis: (a) Tasker, S. Z.; Standley, E. A.;
Jamison, T. F. Nature 2014, 509, 299. (b) Mesganaw, T.; Garg, N.
K. Org. Process Res. Dev. 2013, 17, 29. (c) Rosen, B. M.; Quasdorf,
K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A. M.; Garg, N. K.;
Percec, V. Chem. Rev. 2011, 111, 1346. Select examples: (d) Tang,
Z. Y.; Hu, Q. S. J. Am. Chem. Soc. 2004, 126, 3058. (e) Xing, C. H.;
Lee, J. R.; Tang, Z. Y.; Zheng, J. R.; Hu, Q. S. Adv. Synth. Catal. 2011,
353, 2011. (f) Chen, W. B.; Xing, C. H.; Dong, J.; Hu, Q. S. Adv.
Synth. Catal. 2016, 358, 2072. (g) Guan, B. T.; Wang, Y.; Li, B. J.;
Yu, D. G.; Shi, Z. J. J. Am. Chem. Soc. 2008, 130, 14468.
(h) Quasdorf, K. W.; Tian, X.; Garg, N. K. J. Am. Chem. Soc. 2008,
130, 14422. (i) Muto, K.; Yamaguchi, J.; Musaev, D. G.; Itami, K.
Nat. Commun. 2015, 6, 7508. (j) Correa, A.; Leon, T.; Martin, R.
J. Am. Chem. Soc. 2014, 136, 1062. (k) Tobisu, M.; Shimasaki, T.;
Chatani, N. Angew. Chem. Int. Ed. 2008, 47, 4866. (l) Yang, J.;
Chen, T.; Han, L. B. J. Am. Chem. Soc. 2015, 137, 1782. (m) Zhou,
Q.; Cobb, K. M.; Tan, T.; Watson, M. P. J. Am. Chem. Soc. 2016,
138, 12057. (n) Erickson, L. W.; Lucas, E. L.; Tollefson, E. J.; Jarvo,
E. R. J. Am. Chem. Soc. 2016, 138, 14006.
(17) At present, only 3 general methods for room-temperature N–C
amide bond cross-coupling have been reported. See, refs. 3d, 6a,
and 6c. See also ref. 8j.
(18) (a) Jabeen, I.; Pleban, K.; Rinner, U.; Chiba, P.; Ecker, G. F. J. Med.
Chem. 2012, 55, 3261. (b) Sharmoukh, W.; Kol, K. C.; Noh, C.;
Lee, J. Y.; Son, S. U. J. Org. Chem. 2010, 75, 6708. (c) Kameswaran,
V. Patent WO2001051440 A1, 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.
Int. Ed. 2017, 56, 3972. (i) For an excellent de-hydroamidocarbo-
nylation, see: Hu, J.; Wang, M.; Pu, X.; Shi, Z. Nat. Commun.
2
cinimides, see: Amani, J.; Alam, R.; Badir, S.; Molander, G. A. Org.
Lett. 2017, 19, 2426. (k) For reductive coupling of N-acylglu-
tarimides, see: Ni, S.; Zhang, W.; Mei, H.; Han, J.; Pan, Y. Org.
Lett. 2017, 19, 2536.
017, 8, 14993. (j) For Ni/photoredox coupling using N-acylsuc-
(
9) For metal-free reactions by resonance destabilization controlled
amide bond N–C activation, see: (a) Liu, Y.; Meng, G.; Liu, R.;
Szostak, M. Chem. Commun. 2016, 52, 6841. (b) Liu, Y.; Liu, R.;
Szostak, M. Org. Biomol. Chem. 2017, 15, 1780. (c) Liu, Y.; Shi, S.;
Achtenhagen, M.; Liu, R.; Szostak, M. Org. Lett. 2017, 19, 1614.
For N–C activation by amide pyramidalization, see: (d) Liu, C.;
Achtenhagen, M.; Szostak, M. Org. Lett. 2016, 18, 2375.
10) Review on acyl-metal intermediates: Gooßen, L. J.; Rodriguez,
N.; Gooßen, K. Angew. Chem. Int. Ed. 2008, 47, 3100.
11) (a) Review on electrophilic activation of amides: Kaiser, D.;
Maulide, N. J. Org. Chem. 2016, 81, 4421. (b) For an excellent
overview of amide cross-coupling, see: Ruider, S. A.; Maulide, N.
Angew. Chem. Int. Ed. 2015, 54, 13856.
(
(
(
12) For leading references on twisted bridged amides, see: (a) Tani,
K.; Stoltz, B. M. Nature 2006, 441, 731. (b) Greenberg, A.;
Venanzi, C. A. J. Am. Chem. Soc. 1993, 115, 6951. (c) Szostak, R.;
Aubé, J.; Szostak, M. Chem. Commun. 2015, 51, 6395.
(
(
(
13) Several suppliers list succinimide for < $ 0.05/g. In bulk, succin-
imide is available for < $ 0.01/g. Accessed 03/20/2017.
14) Note that scission of the N–Z bond (Z = activating group) is a
major side reaction in amide bond cross-coupling.
15) Reviews on Negishi cross-coupling: (a) Haas, D.; Hammann, J.
M.; Greiner, R.; Knochel, P. ACS Catal. 2016, 6, 1540.
(19) Phapale, V. B.; Cardenas, D. J. Chem. Soc. Rev. 2009, 38, 1598.
(20) For a review on nucleophilic reactivity of organozinc reagents,
see: Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
(
b) Benischke, A. D.; Ellwart, M.; Becker, M. R.; Knochel, P. Syn-
(21) N-Acylsuccinimides are crystalline, bench-stable solids, with no
decomposition observed when stored on an open bench-top at
ambient conditions for periods >12 months.
thesis 2016, 48, 1101. (c) Handbook of Functionalized Organome-
tallics; Knochel, P., Ed.; Wiley-VCH: Weinheim, 2005. (d) Klatt,
T.; Markiewicz, J. T.; Sämann, C.; Knochel, P. J. Org. Chem. 2014,
©
Georg Thieme Verlag Stuttgart · New York — Synthesis 2017, 49, A–G