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ChemComm
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COMMUNICATION
Journal Name
(a)
OMe
(h) G. Meng and M. Szostak, Org. LettD.,O2I:01108.1,02309/,C697C8C90-46673943H;
(i) J. Wang, M. Shang, H. Lundberg, K. S. Feu, S. J. Hecker, T.
Qin, D. G. Blackmond and P. S. Baran, ACS Catal., 2018, 8,
9537-9542.
X. Zheng, J. Ding, J. Chen, W. Gao, M. Liu and H. Wu, Org. Lett.,
2011, 13, 1726-1729.
J. Zhang, J. Chen, M. Liu, X. Zheng, J. Ding and H. Wu, Green
Chem., 2012, 14, 912-916.
(a) H. Wang, A. Yu, A. Cao, J. Chang and Y. Wu, Appl.
Organometal. Chem., 2013, 27, 611-614; (b) T. Begum, M.
Mondal, M. P. Borpuzari, R. Kar, P. K. Gogoi and U. Bora, Eur.
J. Org. Chem., 2017, 2017, 3244-3248.
(a) S. S. Bahekar, A. P. Sarkate, V. M. Wadhai, P. S. Wakte and
D. B. Shinde, Catal. Commun., 2013, 41, 123-125; (b) H. Tian,
A. Cao, L. Qiao, A. Yu, J. Chang and Y. Wu, Tetrahedron, 2014,
70, 9107-9112; (c) A. Rostami, A. Rostami and A. Ghaderi, J.
Org. Chem., 2015, 80, 8694-8704.
M. R. Yadav, M. Nagaoka, M. Kashihara, R.-L. Zhong, T.
Miyazaki, S. Sakaki and Y. Nakao, J. Am. Chem. Soc., 2017, 139,
9423-9426.
NO2
B(OH)2
standard
condition
F
MeO
F
1.0 g
1.61 g
(10.59 mmol)
5
6
7
(7.09 mmol)
1.18 g, 82% yield
O
O
B(OH)2
MeO
OEt
8
(b)
NO2
N
H
N1, 73% yield
standard
condition
O
O
MeO
OEt
9
N
H
O
O
B(OH)2
10 F. Inoue, M. Kashihara, M. R. Yadav and Y. Nakao, Angew.
Chem. Int. Ed., 2017, 56, 13307-13309.
11 R.-L. Zhong, M. Nagaoka, Y. Nakao and S. Sakaki,
Organometallics, 2018, 37, 3480-3487.
12 Y. Wang, Q. Ye, G. Qiu and J.-B. Liu, Chin. J. Org. Chem., 2018,
38, 1650-1655.
Nitrendipine
MeO
OEt
N
H
N2, 30% yield
Modification of Nitrendipine
13 S. Nolan and C. Cazin, Science of Synthesis: N-Heterocyclic
Carbenes in Catalytic Organic Synthesis, Georg Thieme Verlag,
2017.
Scheme 1. Gram scale experiment and derivatization of the
pharmaceutical products.
14 (a) E. A. B. Kantchev, C. J. O'Brien and M. G. Organ, Angew.
Chem. Int. Ed., 2007, 46, 2768-2813; (b) T. Ben Halima, W.
Zhang, I. Yalaoui, X. Hong, Y.-F. Yang, K. N. Houk and S. G.
Newman, J. Am. Chem. Soc., 2017, 139, 1311-1318; (c) G.
Meng and M. Szostak, Org. Lett., 2018, 20, 6789-6793.
15 (a) A. Chartoire, X. Frogneux, A. Boreux, A. M. Slawin and S.
P. Nolan, Organometallics, 2012, 31, 6947-6951; (b) Y.-L.
Zheng and S. G. Newman, ACS Catal., 2019, 9, 4426-4433; (c)
S. Shi, S. P. Nolan and M. Szostak, Acc. Chem. Res., 2018, 51,
2589-2599; (d) N. Fukaya, T. Mizusaki, K. Hatakeyama, Y. Seo,
Y. Inaba, K. Matsumoto, V. Y. Lee, Y. Takagi, J. Kuwabara and
T. Kanbara, Organometallics, 2018, 38, 375-384.
16 (a) G. Xu, C. H. Senanayake and W. Tang, Acc. Chem. Res.,
2019, 52, 1101-1112; (b) S. Handa, M. P. Andersson, F. Gallou,
J. Reilly and B. H. Lipshutz, Angew. Chem. Int. Ed., 2016, 55,
4914-4918; (c) D. S. Surry and S. L. Buchwald, Chem. Sci., 2011,
2, 27-50; (d) J. Yin, M. P. Rainka, X.-X. Zhang and S. L.
Buchwald, J. Am. Chem. Soc., 2002, 124, 1162-1163.
17 (a) S. Gu and W. Chen, Organometallics, 2009, 28, 909-914;
(b) X. Zhang, B. Liu, A. Liu, W. Xie and W. Chen,
Organometallics, 2009, 28, 1336-1349; (c) B. Liu, Q. Xia and
W. Chen, Angew. Chem. Int. Ed., 2009, 48, 5513-5516; (d) C.
Chen, H. Qiu and W. Chen, Inorg. Chem., 2011, 50, 8671-8678.
18 Y. Kim, Y. Kim, M. Y. Hur and E. Lee, J. Organomet. Chem.,
2016, 820, 1-7.
We thank the National Natural Science Foundation (NSF) of
China (21572203 and 21472140) and the NSF of Zhejiang
Province (LZ16B020001) for financial support.
Conflicts of interest
The authors declare no competing financial interest.
Notes and references
1
(a) P. C. Kearney and D. D. Kaufman, Herbicides: chemistry,
degradation and mode of action, Marcel Dekker, Inc., 1975;
(b) H. Zollinger, Color chemistry: syntheses, properties, and
applications of organic dyes and pigments, John Wiley & Sons,
2003; (c) K. Lee and R. Tsien, Nature, 1983, 302, 790-794; (d)
M.-P. Belciug and V. S. Ananthanarayanan, J. Med. Chem.,
1994, 37, 4392-4399.
2
3
Y. Yang, Angew. Chem. Int. Ed., 2017, 56, 15802-15804.
(a) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457-
2483; (b) R. A. Swyka, W. G. Shuler, B. J. Spinello, W. Zhang, C.
Lan and M. J. Krische, J. Am. Chem. Soc., 2019, 141, 6864-
6868; (c) Z. Chen, Y. Jiang, L. Zhang, Y.-L. Guo and D. Ma, J. Am.
Chem. Soc., 2019, 141, 3541-3549; (d) J. Clark, M. Ferguson,
R. McDonald and M. Stradiotto, Angew. Chem. Int. Ed., 2019,
58, 6391-6395.
(a) C. M. Lavoie and M. Stradiotto, ACS Catal., 2018, 8, 7228-
7250; (b) D. A. Watson, M. Su, G. Teverovskiy, Y. Zhang, J.
García-Fortanet, T. Kinzel and S. L. Buchwald, Science, 2009,
325, 1661-1664; (c) S. T. Keaveney, G. Kundu and F.
Schoenebeck, Angew. Chem. Int. Ed., 2018, 130, 12753-
12757; (d) Y. Ye, T. Takada and S. L. Buchwald, Angew. Chem.
Int. Ed., 2016, 55, 15559-15563; (e) S. M. King and S. L.
Buchwald, Org. Lett., 2016, 18, 4128-4131; (f) D.-G. Yu, B.-J. Li
and Z.-J. Shi, Acc. Chem. Res., 2010, 43, 1486-1495; (g) T. Ben
Halima, W. Zhang, I. Yalaoui, X. Hong, Y.-F. Yang, K. N. Houk
19 B. P. Fors and S. L. Buchwald, J. Am. Chem. Soc., 2009, 131,
12898-12899.
20 Z. Shen, C. Rowlings, B. Kerr, V. Hingorani, K. Manhard, B.
Quart, L.-T. Yeh and C. Storgard, Drug Design. Dev. Ther.,
2015, 9, 3423-3434.
4
4 | J. Name., 2012, 00, 1-3
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