Journal of the American Chemical Society
Page 4 of 6
Alley, M. R.; Sanders, V.; Plattner, J. J. J. Med. Chem. 2006, 49,
4447.
Chem., Int. Ed. 2008, 47, 6414. (i) Barker, T. J.; Jarvo, E. R. J.
1
2
3
4
5
6
7
8
Am. Chem. Soc. 2009, 131, 15598. (j) Hatakeyama, T.;
Yoshimoto, Y.; Ghorai, S. K.; Nakamura, M. Org. Lett. 2010, 12,
1516. (k) Rucker, R. P.; Whittaker, A. M.; Dang, H.; Lalic, G. J.
Am. Chem. Soc. 2012, 134, 6571. (l) Grohmann, C.; Wang, H.;
Glorius, F. Org. Lett. 2012, 14, 656. (m) Xiao, Q.; Tian, L.; Tan,
R.; Xia, Y.; Qiu, D.; Zhang, Y.; Wang, J. Org. Lett. 2012, 14,
4230. (n) Mlynarski, S. N.; Karns, A. S.; Morken, J. P. J. Am.
Chem. Soc. 2012, 134, 16449. (o) Zhu, C.; Li, G.; Ess, D. H.;
Falck, J. R.; Kürti, L. J. Am. Chem. Soc. 2012, 134, 18253. (p)
Miura, T.; Morimoto, M.; Murakami, M. Org. Lett. 2012, 14,
5214. (q) Qian, X.; Yu, Z.; Auffrant, A.; Gosmini, C. Chem. Eur.
J. 2013, 19, 6225. (r) Dong, Z.; Dong, G. J. Am. Chem. Soc.
2013, 135, 18350. (s) Matsubara, T.; Asako, S.; Ilies, L.;
Nakamura, E. J. Am. Chem. Soc. 2014, 136, 646. (t) McDonald,
S. L.; Wang, Q. Angew. Chem., Int. Ed. 2014, 53, 1867. (u) Patel,
P.; Chang, S. Org. Lett. 2014, 16, 3328. (v) Feng, C.; Loh, T.-P.
Org. Lett. 2014, 16, 3444. (w) Zhu, D.; Yang, G.; He, J.; Chu,
L.; Chen, G.; Gong, W.; Chen, K.; Eastgate, M. D.; Yu, J.-Q.
Angew. Chem., Int. Ed. 2015, 54, 2497.
(3) (a) Bross, P. F.; Kane, R.; Farrell, A. T.; Abraham, S.; Benson, K.;
Brower, M. E.; Bradley, S.; Gobburu, J. V.; Goheer, A.; Lee, S.-
L.; Leighton, J.; Liang, C. Y.; Lostritto, R. T.; McGuinn, W. D.;
Morse, L. A.; Verbois, S. L.; Williams, G.; Wang, Y.-C.; Pazdur,
R. Clin. Cancer Res. 2004, 10, 3954. (b) Kupperman, E.; Lee, E.
C.; Cao, Y.; Bannerman, B.; Fitzgerald, M.; Berger, A.; Yu, J.;
Yang, Y.; Hales, P.; Bruzzese, F.; Liu, J.; Blank, J.; Garcia, K.;
Tsu, C.; Dick, L.; Fleming, P.; Yu, L.; Manfredi, M.; Rolfe, M.;
Bolen, J. Cancer Res. 2010, 70, 1970. Also see: (c) Rentsch, A.;
Landsberg, D.; Brodmann, T.; Bülow, L.; Girbig, A.-K.; Kalesse,
M. Angew. Chem., Int. Ed. 2013, 52, 5450.
9
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
(4) (a) Ohmura, T.; Awano, T.; Suginome, M. J. Am. Chem. Soc.
2010, 132, 13191. (b) Awano, T. Ohmura, T.; Suginome, M. J.
Am. Chem. Soc. 2011, 133, 20738.
(5) (a) Brown, H. C.; Singh, S. M.; Rangaishevi, M. V. J. Org. Chem.
1986, 51, 3150. (b) Matteson, D. S. Chem. Rev. 1989, 89, 1535.
(6) (a) He, Z.; Yudin, A. K. J. Am. Chem. Soc. 2011, 133, 13770. (b)
Li, J.; Burke, M. D. J. Am. Chem. Soc. 2011, 133, 13774. (c) He,
Z.; Zajdlik, A.; Denis, J. D. S.; Assem, N.; Yudin, A. K. J. Am.
Chem. Soc. 2012, 134, 9926. (d) Zajdlik, A.; Wang, Z.; Hickey, J.
L.; Aman, A.; Schimmer, A. D.; Yudin, A. K. Angew. Chem., Int.
Ed. 2013, 52, 8411.
(7) (a) Beenen, M. A.; An, C.; Ellman, J. A. J. Am. Chem. Soc. 2008,
130, 6910. (b) Buesking, A. W.; Bacauanu, V.; Cai, I.; Ellman, J.
A. J. Org. Chem. 2014, 79, 3671.
(8) (a) Solé, C.; Gulyás, H.; Fernández, E. Chem. Commun. 2012, 48,
3769. (b) Hong, K.; Morken, J. P. J. Am. Chem. Soc. 2013, 135,
9252. (c) Wamg, D.; Cao, P.; Wang, B.; Jia, T.; Lou, Y.; Wang,
M.; Liao, J. Org. Lett. 2015, 17, 2420.
(9) Reviews on the metal-catalyzed hydroamination: (a) Müller, T. E.;
Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev.
2008, 108, 3795. (b) Fukumoto, Y. J. Synth. Org. Chem., Jpn.
2009, 67, 735. (c) Hesp, K. D.; Stradiotto, M. ChemCatChem
2010, 2, 1192. (d) Hartwig, J. F. Organotransition Metal
Chemistry: From Bonding to Catalysis; University Science
Books: Sausalito, CA, 2010; Vol. 1, p 700. (e) Huang, L.; Arndt,
M.; Gooβen, K.; Heydt, H.; Gooβen, L. J. Chem. Rev. 2015, 115,
2596. (f) Coman, S. M.; Parvulescu, V. I. Org. Process Res. Dev.
2015, 19, 1327. Selected recent examples of the Cu-catalyzed
hydroamination: (g) Taylor, J. G.; Whittall, N.; Hii, K. K. Org.
Lett. 2006, 8, 3561. (h) Munro-Leighton, C.; Delp, S. A.; Blue, E.
D.; Gunnoe, T. B. Organometallics 2007, 26, 1483. (i) Munro-
Leighton, C.; Delp, S. A.; Alsop, N, M.; Blue, E. D.; Gunnoe, T.
B. Chem. Commun. 2008, 111. (j) Ohmiya, H.; Morita, T.;
Sawamura, M. Org. Lett. 2009, 11, 2145. (k) Turnpenny, B. W.;
Hyman, K. L.; Chemler, S. R. Organometallics 2012, 31, 7819.
(10) For organocatalytic approaches, see: (a) Moran, J.; Gorelsky, S.
I.; Dimitrijevic, E.; Lebrun, M.-E.; Bédard, A.-C.; Séguin, C.;
Beauchemin, A. M. J. Am. Chem. Soc. 2008, 130, 17893. (b)
Guimond, N.; MacDonald, M. J.; Lemieux, V.; Beauchemin, A.
M. J. Am. Chem. Soc. 2012, 134, 16571. (c) MacDonald, M. J.;
Hesp, C. R.; Schipper, D. J.; Pesant, M.; Beauchemin, A. M.
Chem.–Eur. J. 2013, 19, 2597.
(13) Our recent publications: (a) Kawano, T.; Hirano, K.; Satoh, T.;
Miura, M. J. Am. Chem. Soc. 2010, 132, 6900. (b) Matsuda, N.;
Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2012,
51, 3642. (c) Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M.
Angew. Chem., Int. Ed. 2012, 51, 11827. (d) Matsuda, N.; Hirano,
K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2013, 135, 4934. (e)
Miki, Y.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int.
Ed. 2013, 52, 10830. (f) Miki, Y.; Hirano, K.; Satoh, T.; Miura,
M. Org. Lett. 2014, 16, 1498. (g) Sakae, R.; Hirano, K.; Satoh,
T.; Miura, M. Angew. Chem., Int. Ed. 2015, 54, 613. (h) Sakae,
R.; Hirano, K.; Miura, M. J. Am. Chem. Soc. 2015, 137, 6460. (i)
Hirano, K.; Miura, M. Pure Appl. Chem. 2014, 86, 291.
(14) (a) Zhu, S.; Niljianskul, N.; Buchwald, S. L. J. Am. Chem. Soc.
2013, 135, 15746. (b) Zhu, S.; Buchwald, S. L. J. Am. Chem. Soc.
2014, 136, 15913. (c) Niljianskul, N.; Zhu, S.; Buchwald, S. L.
Angew. Chem., Int. Ed. 2015, 54, 1638. (d) Shi, S.-L.; Buchwald,
S. L. Nat. Chem. 2015, 7, 38. (e) Yang, Y.; Shi, S.-L.; Niu, D.;
Liu, P.; Buchwald, S. L. Science 2015, 349, 62.
(15) Review: Deutsch, C.; Krause, N.; Lipshutz, B. H. Chem. Rev.
2008, 108, 2916.
(16) Mankad, N. P.; Laitar, D. S.; Sadighi, J. P. Organometallics 2004,
23, 3369.
(17) Dang, Li.; Zhao, H.; Lin, Z.; Marder, T. Organometallics 2007,
26, 2824.
(18) (a) Noguchi, H.; Hojo, K.; Suginome, M. J. Am. Chem. Soc.
2007, 132, 2548.
For Bdan-substituted alkenes as good
acceptors in transition-metal-catalyzed addition reactions, see:
(b) Sasaki, K.; Hayashi, T. Angew. Chem., Int. Ed. 2010, 49,
8145. (c) Feng, X.; Jeon, H.; Yun, J. Angew. Chem., Int. Ed.
2013, 52, 3989.
(19) Under the standard reaction conditions 1a-Bpin and 1a-
B(MIDA) completely decomposed, and any products were not
detected. The former may undergo the transmetalation with
Cu(I) species, and the latter may be hydrolyzed under basic
conditions. See the Supporting Information for details.
(20) In the case of simple styrenes, the opposite regioselectivity was
observed: the amino group was selectively introduced at the
benzylic position. See ref 13e, 14a.
(21) Buchwald reported the hydroamination of simple terminal
alkenes under related conditions; see ref 14b.
(22) (a) Noack, M.; Göttlich, R. Chem. Commun. 2002, 536. Also
see: (b) Tsuritani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2001,
3, 2709. (c) Tsuritani, T.; Shinokubo, H.; Oshima, K. J. Org.
Chem. 2003, 68, 3246.
(11) Hartwig reported
a
C-H borylation approach to α-
aminoboronates. (a) Li, Q.; Liskey, C. W.; Hartwig, J. F. J. Am.
Chem. Soc. 2014, 136, 8755. In the course of this study, Tang
reported a Rh-catalyzed enantioselective hydroboration approach
to optically active α-amino tertiary boronic acids. (b) Hu, N.;
Zhao, G.; Zhang, Y.; Liu, X.; Li, G.; Tang, W. J. Am. Chem. Soc.
2015, 137, 6746.
(12) Reviews: (a) Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947. (b)
Narasaka, K.; Kitamura, M. Eur. J. Org. Chem. 2005, 21, 4505.
(c) Ciganek, E. Org. React. 2009, 72, 1. (d) Barker, T. J.; Jarvo,
E. R. Synthesis 2011, 3954. Recent examples: (e) Berman, A.
M.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 5680. (f)
Campbell, M. J.; Johnson, J. S. Org. Lett. 2007, 9, 1521. (g) Liu,
S.; Liebeskind, L. S. J. Am. Chem. Soc. 2008, 130, 6918. (h) He,
C.; Chen, C.; Cheng, J.; Liu, C.; Liu, W.; Li, Q.; Lei, A. Angew.
(23) Crystallographic data for the structure of 3ih has been deposited
with the Cambridge Crystallographic Data Center (CCDC
1425245). See the Supporting Information for details.
(24) The 3jk-Bpin was relatively unstable under chiral HPLC
analytical conditions, and thus the correct er value could not be
ACS Paragon Plus Environment