10.1002/adsc.201701497
Advanced Synthesis & Catalysis
Jiang, X. Mao, B. Zhang, H. Liu, Q. Yu, J. Med. Chem.
2005, 48, 7208.
Fujita, J. Ichikawa, Org. Lett. 2015, 17, 1126. d) L.
Kong, X. Zhou, X. Li, Org. Lett. 2016, 18, 6320.
[2] For representative reviews, see: a) G. Landelle, M.
Bergeron, M.-O. Turcotte-Savard, J.-F. Paquin, Chem.
Soc. Rev. 2011, 40 , 2867. b) H. Yanai, T. Taguchi, Eur.
J. Org. Chem. 2011, 5939. For selected examples, see:
c) M. Bergeron, T. Johnson, J.-F. Paquin, Angew. Chem.
Int. Ed. 2011, 50, 11112. d) Q. Liu, X. Shen, C. Ni, J.
Hu, Angew. Chem. Int. Ed. 2017, 56, 619. e) W. Zhang,
W. Huang, J. Hu, Angew. Chem. Int. Ed. 2009, 48,
9858. f) H. Sommer, A. Fürstner, Chem. Eur. J. 2017,
23, 558. g) M. Michida, T. Mukaiyama, Chem. Lett.
2008, 37, 890. h) Y. Zhao, F. Jiang, J. Hu, J. Am. Chem.
Soc. 2015, 137, 5199.
[13] J. Xie, J. Yu, M. Rudolph, F. Rominger, A. S. K.
Hashmi, Angew. Chem. Int. Ed. 2016, 55, 9416.
[14] a) J.-Q. Wu, S.-S. Zhang, H. Gao, Z. Qi, C.-J. Zhou,
W.-W. Ji, Y. Liu, Y. Chen, Q. Li, X. Li, H. Wang, J.
Am. Chem. Soc. 2017, 139, 3537. b) W.-W. Ji, E. Lin,
Q. Li, H. Wang, Chem. Commun. 2017, 53, 5665.
[15] a) C. Jarava-Barrera, A. Parra, A. López, F. Cruz-
Acosta, D. Collado-Sanz, D. J. Cárdenas, M. Tortosa,
ACS Catal. 2016, 6, 442. b) T. J. Mazzacano, N. P.
Mankad, ACS Catal. 2017, 7, 146. c) M. Guisán-Ceinos,
A. Parra, V. Martín-Heras, M. Tortosa, Angew. Chem.
Int. Ed. 2016, 55, 6969. d) K. Kato, K. Hirano, M.
Miura, Angew. Chem. Int. Ed. 2016, 55, 14400. e) K.
Kubota, K. Hayama, H. Iwamoto, H. Ito, Angew. Chem.
Int. Ed. 2015, 54, 8809. f) W. Su, T.-J. Gong, X. Lu,
M.-Y. Xu, C.-G. Yu, Z.-Y. Xu, H.-Z. Yu, B. Xiao, Y.
Fu, Angew. Chem. Int. Ed. 2015, 54, 12957. g) N.
Matsuda, K. Hirano, T. Satoh, M. Miura, J. Am. Chem.
Soc. 2013, 135, 4934.
[3] a) Boronic Acids: Preparation and Applications in
Organic Synthesis Medicine and Materials (Ed.: D. G.
Hall), Wiley-VCH, Weinheim, 2011. b) J. F. Hartwig,
Acc. Chem. Res. 2012, 45, 864.
[4] a) V. V. Bardin, N. Y. Adonin, H.-J. Frohn, J. Fluor.
Chem. 2012, 135, 114. b) H.-J. Frohn, V. V. Bardin, J.
Organomet. Chem. 2001, 631, 54. c) V. V. Bardin, N.
Y. Adonin, H.-J. Frohn, Z. Für Anorg. Allg. Chem.
2012, 638, 565. d) H.-J. Frohn, V. V. Bardin, Z. Für
Anorg. Allg. Chem. 2001, 627, 2499.
[16] a) R. Doi, M. Ohashi, S. Ogoshi, Angew. Chem. Int.
Ed. 2016, 55, 341. b) Z. Zhang, Q. Zhou, W. Yu, T. Li,
Y. Zhang, J. Wang, Chin. J. Chem. 2017, 35, 387. c) M.
Hu, Z. He, B. Gao, L. Li, C. Ni, J. Hu, J. Am. Chem.
Soc. 2013, 135, 17302. d) Z. Zhang, Q. Zhou, W. Yu, T.
Li, G. Wu, Y. Zhang, J. Wang, Org. Lett. 2015, 17,
2474.
[5] a) E. Clot, O. Eisenstein, N. Jasim, S. A. Macgregor, J.
E. McGrady, R. N. Perutz, Acc. Chem. Res. 2011, 44,
333. b) T. Ahrens, J. Kohlmann, M. Ahrens, T. Braun,
Chem. Rev. 2015, 115, 931. c) Z. Chen, C.-Y. He, Z.
Yin, L. Chen, Y. He, X. Zhang, Angew. Chem. Int. Ed.
2013, 52, 5813. d) T. Braun, M. Ahijado Salomon, K.
Altenhöner, M. Teltewskoi, S. Hinze, Angew. Chem.
Int. Ed. 2009, 48, 1818. e) J. Zhou, M. W. Kuntze-
Fechner, R. Bertermann, U. S. D. Paul, J. H. J. Berthel,
A. Friedrich, Z. Du, T. B. Marder, U. Radius, J. Am.
Chem. Soc. 2016, 138, 5250.
[17] For representative catalytic borylation of C-F bond,
see: a) R. J. Lindup, T. B. Marder, R. N. Perutz, A. C.
Whitwood, Chem. Commun. 2007, 3664. b) T. Braun,
M. Ahijado Salomon, K. Altenhöner, M. Teltewskoi, S.
Hinze, Angew. Chem. Int. Ed. 2009, 48, 1818. c) M.
Teltewskoi, J. A. Panetier, S. A. Macgregor, T. Braun,
Angew. Chem. Int. Ed. 2010, 49, 3947. d) W.-H. Guo,
Q.-Q. Min, J.-W. Gu, X. Zhang, Angew. Chem. Int. Ed.
2015, 54, 9075. e) S. I. Kalläne, M. Teltewskoi, T.
Braun, B. Braun, Organometallics 2015, 34, 1156. f)
X.-W. Liu, J. Echavarren, C. Zarate, R. Martin, J. Am.
Chem. Soc. 2015, 137, 12470. g) T. Niwa, H. Ochiai, Y.
Watanabe, T. Hosoya, J. Am. Chem. Soc. 2015, 137,
14313. h) K. Chen, M. S. Cheung, Z. Lin, P. Li, Org.
Chem. Front. 2016, 3, 875. i) W. Chen, C. Bakewell, M.
Crimmin, Synthesis 2016, 49, 810. j) J. Zhou, M. W.
Kuntze-Fechner, R. Bertermann, U. S. D. Paul, J. H. J.
Berthel, A. Friedrich, Z. Du, T. B. Marder, U. Radius, J.
Am. Chem. Soc. 2016, 138, 5250. k) R. Kojima, K.
Kubota, H. Ito, Chem. Commun. 2017, 53, 10688. l) K.
Kubota, H. Iwamoto, H. Ito, Org. Biomol. Chem. 2017,
15, 285. m) H. Sakaguchi, Y. Uetake, M. Ohashi, T.
Niwa, S. Ogoshi, T. Hosoya, J. Am. Chem. Soc. 2017,
139, 12855.
[6] C. P. Qian, T. Nakai, D. A. Dixon, B. E. Smart, J. Am.
Chem. Soc. 1990, 112, 4602.
[7] X. Huang, P. He, G. Shi, J. Org. Chem. 2000, 65, 627.
[8] a) V. V. Rudyuk, D. V. Fedyuk, L. M. Yagupolskii, J.
Fluor. Chem. 2004, 125, 1465. b) E. Ausekle, S. A.
Ejaz, S. U. Khan, P. Ehlers, A. Villinger, J. Lecka, J.
Sévigny, J. Iqbal, P. Langer, Org. Biomol. Chem. 2016,
14, 11402.
[9] a) C. M. Timperley, J. Fluor. Chem. 2004, 125, 685. b)
D. L. Orsi, B. J. Easley, A. M. Lick, R. A. Altman, Org.
Lett. 2017, 19, 1570. c) M. S. Kim, I. H. Jeong,
Tetrahedron Lett. 2005, 46, 3545.
[10] J. Zhang, C. Xu, W. Wu, S. Cao, Chem. Eur. J. 2016,
22, 9902.
[11] a) W. Dai, X. Zhang, J. Zhang, Y. Lin, S. Cao, Adv.
Synth. Catal. 2016, 358, 183. b) R. T. Thornbury, F. D.
Toste, Angew. Chem. Int. Ed. 2016, 55, 11629. c) W.
Dai, H. Shi, X. Zhao, S. Cao, Org. Lett. 2016, 18, 4284.
[18] During the preparation and revision of this work,
several related work was published: a) J. Zhang, W.
Dai, Q. Liu, S. Cao, Org. Lett. 2017, 19, 3283. b) H.
Sakaguchi, Y. Uetake, M. Ohashi, T. Niwa, S. Ogoshi,
T. Hosoya, J. Am. Chem. Soc. 2017, 139, 12855–12862.
c) H. Sakaguchi, M. Ohashi, S. Ogoshi, Angew. Chem.
Int. Ed. 2017. doi: 10.1002/anie.201710866
[12] a) D. Zell, U. Dhawa, V. Müller, M. Bursch, S.
Grimme, L. Ackermann, ACS Catal. 2017, 7, 4209. b)
P. Tian, C. Feng, T.-P. Loh, Nat. Commun. 2015, 6,
7472. c) K. Fuchibe, T. Morikawa, K. Shigeno, T.
5
This article is protected by copyright. All rights reserved.