COMMUNICATIONS
mixture was diluted with EtOAc, passed through Celite and
the filter cake was then rinsed with EtOAc (ca. 40 mL in
total). The filtrate was removed under vacuum to afford the
crude mixture which was purified by flash column chroma-
tography and/or recrystallization to furnish the desired prod-
uct.
[10] a) G. A. Molander, S. L. J. Trice, S. M. Kennedy, J. Org.
Chem. 2012, 77, 8678–8688; b) G. A. Molander, S. L. J.
Trice, S. M. Kennedy, S. D. Dreher, M. T. Tudge, J. Am.
Chem. Soc. 2012, 134, 11667–11673; c) G. A. Molander,
S. L. J. Trice, S. D. Dreher, J. Am. Chem. Soc. 2010, 132,
17701–17703.
[11] a) T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem.
1995, 60, 7508–7510; b) N. Miyaura, A. Suzuki, Chem.
Rev. 1995, 95, 2457–2483.
[12] a) M. Murata, S. Watanabe, Y. Masuda, J. Org. Chem.
1997, 62, 6458–6459; b) M. Murata, T. Oyama, S. Wata-
nabe, Y. Masuda, J. Org. Chem. 2000, 65, 164–168.
[13] G. A. Molander, S. L. J. Trice, B. Tschaen, Tetrahedron
2015, 71, 5758–5764.
[14] A. M. Mak, Y. H. Lim, H. Jong, Y. Yang, C. W. Jo-
hannes, E. G. Robins, M. B. Sullivan, Organometallics
2016, 35, 1036–1045.
[15] F.-F. Yong, W. Wu, A. M. Mak, M. B. Sullivan, E. G.
Robins, C. W. Johannes, H. Jong, Y. H. Lim, manuscript
under revision. 2016.
[16] W.-K. Chow, C.-M. So, C.-P. Lau, F.-Y. Kwong, Chem.
Eur. J. 2011, 17, 6913–6917, (S6913/1–S6913/47).
[17] J. Magano, J. R. Dunetz, Chem. Rev. 2011, 111, 2177–
2250.
[18] a) D. S. Surry, S. L. Buchwald, Angew. Chem. 2008, 120,
6438–6461; Angew. Chem. Int. Ed. 2008, 47, 6338–6361;
b) D. S. Surry, S. L. Buchwald, Chem. Sci. 2011, 2, 27–
50.
[19] a) C. C. Mauger, G. A. Mignani, Org. Proc. Res. Dev.
2004, 8, 1065–1071; b) S. L. Buchwald, C. Mauger, G.
Mignani, U. Scholzc, Adv. Synth. Catal. 2006, 348, 23–
39; c) C. Mauger, G. Mignani, Adv. Synth. Catal. 2005,
347, 773–782; d) C. Mauger, G. Mignani, Synth.
Commun. 2005, 36, 1123–1129; e) R. R. Poondra, N. J.
Turner, Org. Lett. 2005, 7, 863–866.
[20] a) V. Pandarus, G. v. Gingras, F. O. Bꢂland, R. Cirimin-
na, M. Pagliaro, Org. Process Res. Dev. 2014, 18, 1550–
1555; b) R. Ciriminna, V. Pandarus, F. Bꢂland, M. Pa-
gliaro, Catal. Sci. Technol. 2016, 6, 4678–4685.
[21] a) B. P. Fors, P. Krattiger, E. Strieter, S. L. Buchwald,
Org. Lett. 2008, 10, 3505–3508; b) B. P. Fors, K. Doole-
weerdt, Q. Zeng, S. L. Buchwald, Tetrahedron 2009, 65,
6576–6583; c) K. Dooleweerdt, B. P. Fors, S. L. Buch-
wald, Org. Lett. 2010, 12, 2350–2353; d) C. Amatore, A.
Jutand, M. A. M’Barki, Organometallics 1992, 11,
3009–3013; e) F. Ozawa, A. Kubo, T. Hayashi, Chem.
Lett. 1992, 2177–2180.
[22] a) S. Tasler, J. Mies, M. Langa, Adv. Synth. Catal. 2007,
349, 2286–2300; b) Q. Zhang, Z. Xia, M. J. Mitten,
L. M. Lasko, V. Klinghofer, J. Bouska, E. F. Johnson,
T. D. Penning, Y. Luo, V. L. Giranda, A. R. Shoemaker,
K. D. Stewart, S. W. Djuric, A. Vasudevan, Bioorg.
Med. Chem. Lett. 2012, 22, 7615–7622; c) L. Xu, P. Li,
Chem. Commun. 2015, 51, 5656–5659; d) C. D. Haffner,
J. D. Becherer, E. E. Boros, R. Cadilla, T. Carpenter,
D. Cowan, D. N. Deaton, Y. Guo, W. Harrington, B. R.
Henke, M. R. Jeune, I. Kaldor, N. Milliken, K. G.
Petrov, F. Preugschat, C. Schulte, B. G. Shearer, T.
Shearer, T. L. Smalley, E. L. Stewart, J. D. Stuart, J. C.
Ulrich, J. Med. Chem. 2015, 58, 3548–3571.
Acknowledgements
The authors thank Nurhanisah Binte Kamarudin for her val-
uable contributions to facilitate the development of the
Suzuki–Miyaura cross-coupling methodology, as well as the
analytical facilities at ICES for the HR-MS data. Financial
support for this work was provided by the A*STAR Institute
of Chemical and Engineering Sciences (ICES) and the
A*STAR Singapore Bioimaging Consortium (SBIC).
References
[1] D. W. Tay, H. Jong, Y. H. Lim, W. Wu, X. Chew, E. G.
Robins, C. W. Johannes, J. Org. Chem. 2015, 80, 4054–
4063.
[2] a) Y. Yang, X. Chew, C. W. Johannes, E. G. Robins, H.
Jong, Y. H. Lim, Eur. J. Org. Chem. 2014, 7184–7192;
b) Y. Yang, J. F. Y. Lim, X. Chew, E. G. Robins, C. W.
Johannes, Y. H. Lim, H. Jong, Catal. Sci. Technol. 2015,
5, 3501–3506.
[3] a) T. Ishiyama, Y. Itoh, T. Kitano, N. Miyaura, Tetrahe-
dron Lett. 1997, 38, 3447–3450; b) A. Giroux, Y. Han,
P. Prasit, Tetrahedron Lett. 1997, 38, 3841–3844.
[4] a) W. K. Chow, O. Y. Yuen, P. Y. Choy, C. M. So, C. P.
Lau, W. T. Wong, F. Y. Kwong, RSC Adv. 2013, 3,
12518–12539; b) T. Martin, C. Laguerre, C. Hoarau, F.
Marsais, Org. Lett. 2009, 11, 3690–3693; c) A. Hooper,
A. Zambon, C. J. Springer, Org. Biomol. Chem. 2016,
14, 963–969; d) B. H. Lipshutz, R. Moser, K. R. Voig-
tritter, Isr. J. Chem. 2010, 50, 691–695; e) M. Miura, T.
Koike, T. Ishihara, F. Hirayama, S. Sakamoto, M.
Okada, M. Ohta, S.-i. Tsukamoto, Synth. Commun.
2006, 36, 3809–3820; f) M. Miura, T. Koike, T. Ishihara,
S. Sakamoto, M. Okada, M. Ohta, S.-i. Tsukamoto,
Synth. Commun. 2007, 37, 667–674; g) O. Baudoin, D.
Guenard, F. Gueritte, J. Org. Chem. 2000, 65, 9268–
9271; h) O. Baudoin, M. Cesario, D. Guenard, F. Gue-
ritte, J. Org. Chem. 2002, 67, 1199–1207.
[5] L. Wang, X. Cui, J. Li, Y. Wu, Z. Zhu, Y. Wu, Eur. J.
Org. Chem. 2012, 595–603 (S595/1–S595/35).
[6] K. L. Billingsley, T. E. Barder, S. L. Buchwald, Angew.
Chem. 2007, 119, 5455–5459; Angew. Chem. Int. Ed.
2007, 46, 5359–5363.
[7] W. K. Chow, O. Y. Yuen, C. M. So, W. T. Wong, F. Y.
Kwong, J. Org. Chem. 2012, 77, 3543–3548.
[8] Y. Zhang, J. Gao, W. Li, H. Lee, B. Z. Lu, C. H. Sena-
nayake, J. Org. Chem. 2011, 76, 6394–6400.
[9] a) Y. Chen, H. Peng, Y.-X. Pi, T. Meng, Z.-Y. Lian, M.-
Q. Yan, Y. Liu, S.-H. Liu, G.-A. Yu, Org. Biomol.
Chem. 2015, 13, 3236–3242; b) D. Xie, R. Li, D. Zhang,
J. Hu, D. Xiao, X. Li, Y. Xiang, W. Jin, Tetrahedron
2015, 71, 8871–8875.
Adv. Synth. Catal. 0000, 000, 0 – 0
7
ꢁ 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
ÞÞ
These are not the final page numbers!