Organic Letters
Letter
Ed. 2013, 52, 9896. (j) Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed.
2013, 52, 11726.
(2) For reviews on construction of N-heterocycles by C−H
functionalization, see: (a) Thansandote, P.; Lautens, M. Chem.Eur.
J. 2009, 15, 5874. (b) Mei, T.-S.; Kou, L.; Ma, S.; Engle, K. M.; Yu, J.-
Q. Synthesis 2012, 1778.
(22) (a) Klapars, A.; Parris, S.; Anderson, K. W.; Buchwald, S. L. J.
Am. Chem. Soc. 2004, 126, 3529. (b) Wasserman, H. H.; Matsuyama,
H.; Robinson, R. P. Tetrahedron 2002, 58, 7177.
(3) Selected examples for the synthesis of natural products through
palladium-catalyzed C(sp3)−H functionalization: (a) Feng, Y.; Chen,
G. Angew. Chem., Int. Ed. 2010, 49, 958. (b) Gutekunst, W. R.; Baran,
P. S. J. Am. Chem. Soc. 2011, 133, 19076. (c) Gutekunst, W. R.;
Gianatassio, R.; Baran, P. S. Angew. Chem., Int. Ed. 2012, 51, 7507.
(4) Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14058.
(5) Nadres, E. T.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 7.
(6) He, G.; Zhao, Y.; Zhang, S.; Lu, C.; Chen, G. J. Am. Chem. Soc.
2012, 134, 3.
(7) Ye, X.; He, Z.; Ahmed, T.; Weise, K.; Akhmedov, N. G.; Petersen,
J. L.; Shi, X. Chem. Sci. 2013, 4, 3712.
(8) Zhang, Q.; Chen, K.; Rao, W.; Zhang, Y.; Chen, F.-J.; Shi, B.-F.
Angew. Chem., Int. Ed. 2013, DOI: 10.1002/anie.201306625.
(9) (a) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc.
2005, 127, 13154. (b) Shabashov, D.; Daugulis, O. J. Am. Chem. Soc.
2010, 132, 3965. (c) Tran, L. D.; Daugulis, O. Angew. Chem., Int. Ed.
2012, 51, 5188.
(10) Reddy, B. V. S.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8,
3391.
(11) (a) Feng, Y.; Wang, Y.; Landgraf, B.; Liu, S.; Chen, G. Org. Lett.
2010, 12, 3414. (b) He, G.; Zhang, S.-Y.; Nack, W. A.; Li, Q.; Chen, G.
Angew. Chem., Int. Ed. 2013, 52, 11124.
(12) Ano, Y.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2011, 133,
12984.
(13) Shang, R.; Ilies, L.; Matsumoto, A.; Nakamura, E. J. Am. Chem.
Soc. 2013, 135, 6030.
(14) Pan, F.; Shen, P.-X.; Zhang, L.-S.; Wang, X.; Shi, Z.-J. Org. Lett.
2013, 15, 4758.
(15) Chen, K.; Hu, F.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4,
3906.
(16) For review: Hartwig, J. F. Inorg. Chem. 2007, 46, 1936 and
references cited therein.
(17) A pioneering work by Daugulis9a showed that the arylation of 8-
aminoquinoline-directed carboxamide 1 with 4′-iodoacetophenone
afforded the cross-coupling product 1c in 60% yield accompanied with
a byproduct 1b in 30% yield. Actually, we rechecked this reaction
under the exact condition to find that the byproduct should be β-
lactam 1a, which was identified unambiguously with full spectro-
graphic and X-ray single-crystal analysis.
(18) The CIF files of 1a, 5a, and 7a have been deposited with
Cambridge Crystallographic Data Centre (nos. CCDC 945487,
945489, and 945488). These data can be obtained free of charge
(19) Giri, R.; Maugel, N.; Foxman, B. M.; Yu, J.-Q. Organometallics
2008, 27, 1667.
(20) MK-8712 was showed to have effective activity to inhibit class C
β-lactamases both in vitro and vivo assays. (a) Heinze-Krauss, I.;
Angehrn, P.; Charnas, R. L.; Gubernator, K.; Gutknecht, E.-M.;
Hubschwerlen, C.; Kania, M.; Oefner, C.; Page, M. G. P.; Sogabe, S.;
Specklin, J.-L.; Winkler, F. J. Med. Chem. 1998, 41, 3961. (b) Blizzard,
T. A.; Chen, H.; Kim, S.; Wu, J.; Young, K.; Park, Y. W.; Ogawa, A.;
Raghoobar, S.; Painter, R. E.; Hairston, N.; Lee, S. H.; Misura, A.;
Felcetto, T.; Fitzgerald, P.; Sharma, N.; Lu, J.; Ha, S.; Hickey, E.;
Hermes, J.; Hammond, M. L. Bioorg. Med. Chem. Lett. 2010, 20, 918.
(c) Chen, H.; Blizzard, T. A.; Kim, S.; Wu, J.; Young, K.; Park, Y. W.;
Ogawa, A. M.; Raghoobar, S.; Painter, R. E.; Wisniewski, D.; Hairston,
N.; Fitzgerald, P.; Sharma, N.; Scapin, G.; Lu, J.; Hermes, J.;
Hammond, M. Bioorg. Med. Chem. Lett. 2011, 21, 4267. (d) Blizzard,
T. A.; Chen, H. Y.; Wu, J. Y.; Kim, S.; Ha, S.; Mortko, C. J.;
Variankaval, N.; Chiu, A. WO 2008039420 A2, 2008. (e) Muller, M.;
Wu, X.; Xu, L. WO 2009037229 A1, 2009.
(21) The use of the removable MQ directing group was introduced
by Chen and co-workers, see reference 11b.
483
dx.doi.org/10.1021/ol403364k | Org. Lett. 2014, 16, 480−483