Journal of the American Chemical Society
Page 4 of 5
(6) (a) Lu, Z.; Jun, C.-H.; de Gala, S. R.; Sigalas, M. P.; Eisenstein,
Supporting Information
O.; Crabtree, R. H. Organometallics 1995, 14, 1168. (b) Irvine, G. J.;
Rickard, C. E. F.; Roper, W. R.; Williamson, A.; Wright, L. J. Angew.
Chem. Int. Ed. 2000, 39, 948. (c) Rickard, C. E. F.; Roper, W. R.; Wil-
liamson, A.; Wright, L. J. Organometallics 2002, 21, 1714. (d) Rickard,
C. E. F.; Roper, W. R.; Williamson, A.; Wright, L. J. Organometallics
2002, 21, 4862. (e) Braunschweig, H.; Lutz, M.; Radacki, K. Angew.
Chem. Int. Ed. 2005, 44, 5647. (f) Braunschweig, H.; Kupfer, T.; Lutz,
M.; Radacki, K.; Seeler, F.; Sigritz, R. Angew. Chem. Int. Ed. 2006, 45,
8048. (g) Schubert, H.; Leis, W.; Mayer, H. A.; Wesemann, L. Chem.
Commun. 2014, 50, 2738.
(7) For leading reviews, see: (a) Mkhalid, I. A. I.; Barnard, J. H.;
Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890.
(b) J. F. Hartwig, Acc. Chem. Res. 2012, 45, 864; c) Ros, A.; Fernandez,
R.; Lassaletta, J. M. Chem. Soc. Rev. 2014, 43, 3229. (d) Ishiyama, T.;
Miyaura, N. J. Organomet. Chem. 2003, 680, 3. (e) Hartwig, J. F.
Chem. Soc. Rev. 2011, 40, 1992. (f) Ishiyama, T.; Miyaura, N. Pure Appl.
Chem. 2006, 78, 1369.
(8) For selected references of arene C-H borylation, see: (a) Iver-
son, C. N.; Smith, III M. R. J. Am. Chem. Soc. 1999, 121, 7696. (b) Chen,
H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995.
(c) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.;
Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390. (d) Kawamorita, S.;
Ohmiya, H.; Hara, K.; Fukuoka, A.; Sawamura, M. J. Am. Chem. Soc.
2009, 131, 5058. (e) Mkhalid, I. A. I.; Coventry, D. N.; Jove, D. A.;
Batsanov, A. S.; Howard, J. A. K.; Perutz, R. N.; Marder, T. B. Angew.
Chem. Int. Ed. 2006, 45, 489. (f) Ros, A.; Estepa, B.; López-Rodriguez,
R.; Álvarez, E.; Fernández, R.; Lassaletta, J. M. Angew. Chem. Int. Ed.
2011, 50, 11724. (g) Dai, H. X.; Yu, J. Q. J. Am. Chem. Soc. 2012, 134, 134.
(h) Kawamorita, S.; Murakami, R.; Iwai, T.; Sawamura, M. J. Am.
Chem. Soc. 2013, 135, 2947 (i) Mazzacano, T. J.; Mankad, N. P. J. Am.
Chem. Soc. 2013, 135, 17258. (j) Obligacion, J. V.; Semproni, S. P.;
Chirik, P. J. J. Am. Chem. Soc. 2014, 136, 4133. (k) Dombray, T.;
Werncke, C. G.; Jiang, S.; Grellier, M.; Vendier, L.; Bontemps, S.;
Sortais, J.-B.; Sabo-Etienne, S.; Darcel, C. J. Am. Chem. Soc. 2015, 137,
4062.
1
2
3
4
5
6
7
8
Detailed experimental procedures, spectral data of products
and X-ray crystallographic data for 1 and 3. This material is
AUTHOR INFORMATION
Corresponding Author
9
Author Contributions
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
‡These authors contributed equally.
Notes
The authors declare no competing financial interests.
ACKNOWLEDGMENT
This paper is dedicated to Professor Steve Buchwald on the
occasion of his 60th birthday. We are grateful for financial
support by the National Science Foundation of China (No.
21472146 and No. 21202129) and the Ministry of Science and
Technology of PRC (973 program for young scientists, No.
2014CB548200). We thank Professor Yanzhen Zheng and Mr.
Yousong Ding (FIST) for their help and discussions on X-ray
crystallographic analyses.
REFERENCES
(1) (a) Irvine, G. J.; Lesley, M. J. G.; Marder, T. B.; Norman, N. C.;
Rice, C. R.; Robins, E. G.; Roper, W. R.; Whittell, G. R.; Wright, L. J.
Chem. Rev. 1998, 98, 2685. (b) Aldridge, S.; Coombs, D. L. Coord.
Chem. Rev. 2004, 248, 535. (c) Dang, L.; Lin, Z.; Marder, T. B. Chem.
Commun. 2009, 3987. (d) Braunschweig, H.; Dewhurst, R. D.;
Schneider, A. Chem. Rev. 2010, 110, 3924.
(2) (a) Dettenrieder, N.; Aramaki, Y.; Wolf, B. M. Maichle-
Mössmer, C.; Zhao, X.; Yamashita, M.; Nozaki, K.; Anwander, R.
Angew. Chem. Int. Ed. 2014, 53, 6259. (b) Segawa, Y.; Yamashita, M.;
Nozaki, K. Science 2006, 314, 113. (c) Segawa, Y.; Suzuki, Y.; Yamashi-
ta, M.; Nozaki, K. J. Am. Chem. Soc. 2008, 130, 16069. (d) Zhu, J.; Lin,
Z.; Marder, T. B. Inorg. Chem. 2005, 44, 9384. (e) Braunschweig, H.;
Brenner, P.; Müller, A.; Radacki, K.; Rais, D.; Uttinger, K. Chem. - Eur.
J. 2007, 13, 7171. (f) Braunschweig, H.; Radacki, K.; Uttinger, K. Chem.
- Eur. J. 2008, 14, 7858.
(3) (a) Segawa, Y.; Yamashita, M.; Nozaki, K. J. Am. Chem. Soc.
2009, 131, 9201. (b) Spokoyny, A. M.; Reuter, M. G.; Stern, C. L.; Rat-
ner, M. A.; Seideman, T.; Mirkin, C. A. J. Am. Chem. Soc. 2009, 131,
9482.
(4) (a) For a highlight, see: van der Vlugt, J. I. Angew. Chem. Int. Ed.
2009, 49, 252. (b) Hill, A. F.; Lee, S. B.; Park, J.; Shang, R.; Willis, A. C.
Organometallics 2010, 29, 5661. (c) El-Zaria, M. E.; Arii, H.; Nakamu-
ra, H. Inorg. Chem. 2011, 50, 4149. (d) Hasegawa, M.; Segawa, Y.;
Yamashita, M.; Nozaki, K. Angew. Chem. Int. Ed. 2012, 51, 6956. (e)
Miyada, T.; Yamashita, M. Organometallics 2013, 32, 5281. (f) Hill, A.
F.; McQueen, C. M. A. Organometallics 2014, 33, 1977. (g) Curado, N.;
Maya, C.; Lopez-Serrano, J.; Rodriguez, A. Chem. Commun. 2014, 50,
15718.
(9) Boronic Acids: Preparation and Applications in Organic Synthe-
sis, Medicine and Materials; Hall, D., Ed.; Wiley-VCH, Weinheim,
Germany, 2011.
(10) (a) Preshlock, S. M.; Ghaffari, B.; Maligres, P. E.; Krska, S. W.;
Maleczka, R. E.; Smith, M. R. J. Am. Chem. Soc. 2013, 135, 7572. (b)
Larsen, M. A.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 4287.
(11) (a) Boller, T. M.; Murphy, J. M.; Hapke, M.; Ishiyama, T.;
Miyaura, N.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 14263. (b)
Tamura, H.; Yamazaki, H.; Sato, H.; Sakaki, S. J. Am. Chem. Soc. 2003,
125, 16114. (c) Vanchura, B. A.; Preshlock, S. M.; Roosen, P. C.; Kal-
lepalli, V. A.; Staples, R. J.; Maleczka, R. E.; Singleton, D. A.; Smith, M.
R. Chem. Commun. 2010, 46, 7724. (d) Green, A. G.; Liu, P.; Merlic, C.
A.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 4575.
(12) For bidentate and tridentate silyl ligands in C-H borylation,
see: (a) Ghaffari, B.; Preshlock, S. M.; Plattner, D. L.; Staples, R. J.;
Maligres, P. E.; Krska, S. W.; Maleczka, Jr., R. E.; Smith, III M. R. J.
Am. Chem. Soc. 2014, 136, 14345. (b) Lee, C.-I.; Zhou, J.; Ozerov, O. V.
J. Am. Chem. Soc. 2013, 135, 3560.
(13) For leading references of tetraaminodiborane(4) compounds,
see: (a) Loderer, D.; Noth, H.; Pommerening H.; Rattay, W.; Schick,
H. Chem. Ber. 1994, 127, 1605. (b) Alibadi, M. A.; Batsanov, A. S.;
Bramham, G.; Charmant, J. P.; Haddow, M. F.; Mackay, L.; Mansell, S.
M.; McGrady, J. E.; Norman, N. C.; Roffey, A.; Russell, C. A. Dalton
Trans. 2009, 5348. (c) Xie, X.; Haddow, M. F.; Mansell, S. M.; Nor-
man, N. C.; Russell, C. A. Dalton Trans. 2012, 41, 5348.
(14) (a) Xu, L.; Ding, S.; Li, P. Angew. Chem. Int. Ed. 2014, 53, 1822.
(b) Xu, L.; Li, P. Synlett 2014, 25, 1799. (c) Xu, L.; Li, P. Chem. Com-
mun. 2015, 51, 5656.
(5) (a) Ogawa, H.; Yamashita, M. Dalton Trans. 2013, 42, 625. (b)
Lin, T.-P.; Peters, J. C. J. Am. Chem. Soc. 2013, 135, 15310. (c) Masuda,
Y.; Hasegawa, M.; Yamashita, M.; Nozaki, K.; Ishida, N.; Murakami,
M. J. Am. Chem. Soc. 2013, 135, 7142. (d) Lin, T.-P.; Peters, J. C. J. Am.
Chem. Soc. 2014, 136, 13672. (e) Tsang, M. Y.; Viñas, C.; Teixidor, F.;
Planas, J. G.; Conde, N.; SanMartin, R.; Herrero, M. T.; Domínguez,
E.; Lledós, A.; Vidossich, P.; Choquesillo-Lazarte, D. Inorg. Chem.
2014, 53, 9284.
(15) Paul, S.; Chotana, G. A.; Holmes, D.; Reichle, R. C.; Maleczka,
R. E.; Smith, M. R. J. Am. Chem. Soc. 2006, 128, 15552.
D
ACS Paragon Plus Environment