Journal of the American Chemical Society
Page 4 of 5
Boronat, M.; Corma, A.; González-Arellano, C.; Iglesias, M.; Sánchez,
F. Organometallics 2010, 29, 134.
AUTHOR INFORMATION
1
2
3
4
5
6
7
8
Corresponding Author
(7) Selected examples: (a) Urban, S.; Ortega, N.; Glorius, F. Angew.
Chem., Int. Ed. 2011, 50, 3803. (b) Ortega, N.; Urban, S.; Beiring, B.;
Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 1710. (c) Urban, S.; Beiring,
B.; Ortega, N.; Paul, D.; Glorius, F. J. Am. Chem. Soc. 2012, 134, 15241.
(d) Ortega, N.; Tang, D.-T. D.; Urban, S.; Zhao, D.; Glorius, F. Angew.
Chem., Int. Ed. 2013, 52, 9500. (e) Wysocki, J.; Ortega, N.; Glorius, F.
Angew. Chem., Int. Ed. 2014, 53, 8751. (f) Li, W.; Schlepphorst, C.;
Daniliuc, C.; Glorius, F. Angew. Chem., Int. Ed. 2016, 55, 3300.
(8) (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori,
R. J. Am. Chem. Soc. 1995, 117, 2675. (b) Ohkuma, T.; Ooka, H.;
Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417. (c) Noyori, R.;
Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
(9) (a) Privileged Chiral Ligands and Catalysts; Zhou, Q., Ed.;
Wiley-VCH, Weinhem, Germany, 2011. (b) Zhao, B.; Han, Z.; Ding, K.
Angew. Chem., Int. Ed. 2013, 52, 4744.
(10) Forman, G. S.; Ohkuma, T.; Hems, W. P.; Noyori, R. Tetrahe-
dron Lett. 2000, 41, 9471.
(11) (a) Ohta, T.; Miyake, T.; Seido, N.; Kumobayashi, H.; Takaya,
H. J. Org. Chem. 1995, 60, 357. (b) Kuroki, Y.; Asada, D.; Sakamaki, Y.;
Iseki K. Tetrahedron Lett. 2000, 41, 4603.
(12) Sun, H.; Ho, C. L.; Ding, F.; Soehano, I.; Liu, X. W.; Liang, Z. X.
J. Am. Chem. Soc. 2012, 134, 11924.
(13) (a) Van der Merwe, K. J.; Steyn, P. S.; Fourie, L. Nature 1965,
205, 1112. (b) Malir, F.; Ostry, V.; Pfohl-leszkowicz, A.; Malir, J.; To-
man, J. Toxins 2016, 8, 191.
(14) (a) Itoh, J.; Shomura, T.; Omoto, S.; Miyado, S.; Yuda, Y.; Shi-
bata, U.; Inouye, S. Agric. Biol. Chem. 1982, 46, 1255. (b) Shimojima,
Y.; Hayashi, H.; Ooka, T.; Shibukawa, M.; Iitaka, Y. Tetrahedron 1984,
40, 2519.
(15) For selected examples, see: (a) Islam, M. S.; Ishigami, K.;
Watanabe, H. Tetrahedron 2007, 63, 1074. (b) Chakraborty, T. K.;
Chattopadhyay, A. K. J. Org. Chem. 2008, 73, 3578. (c) Habel, A.;
Boland, W. Org. Biomol. Chem. 2008, 6, 1601. (d) Feng, Y.; Jiang, X.;
De Brabander, J. K. J. Am. Chem. Soc. 2012, 134, 17083.
(16) (a) Fujita, M.; Yoshida, Y.; Miyata, K.; Wakisaka, A.; Sugimura,
T. Angew. Chem., Int. Ed. 2010, 49, 7068. (b) Cornaggia, C.; Manoni,
F.; Torrente, E.; Tallon, S.; Connon, S. J. Org. Lett. 2012, 14, 1850. (c)
Chen, J.; Zhou, L.; Tan, C. K.; Yeung, Y.-Y. J. Org. Chem. 2012, 77, 999.
(d) Suzuki, Y.; Seki, T.; Tanaka, S.; Kitamura, M. J. Am. Chem. Soc.
2015, 137, 9539. (e) Parhi, B.; Maity, S.; Ghorai, P. Org. Lett. 2016, 18,
5220. (f) Woerly, E. M.; Banik, S. M.; Jacobsen, E. N. J. Am. Chem. Soc.
2016, 138, 13858.
(17) For selected reviews, see: (a) Dyson, P. J. Dalton Trans. 2003,
2964. (b) Glorius, F. Org. Biomol. Chem. 2005, 3, 4171. (c) Zhou, Y. G.
Acc. Chem. Res. 2007, 40, 1357. (d) Kuwano, R. Heterocycles 2008, 76,
909. (e) Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev.
2012, 112, 2557. (f) Yu, Z.; Jin, W.; Jiang, Q. Angew. Chem., Int. Ed.
2012, 51, 6060. (g) Zhang, Z.; Buttand, N. A.; Zhang, W. Chem. Rev.
2016, 116, 14769.
(18) Paul, D.; Beiring, B.; Plois, M.; Ortega, N.; Kock, S.; Schlüns,
D.; Neugebauer, J.; Wolf, R.; Glorius, F. Organometallics 2016, 35,
3641.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENT
We are grateful to the Alexander von Humboldt Foundation
(W.L.), the Studienstiftung des Deutschen Volkes (M.P.W.),
and the Deutsche Forschungsgemeinschaft (Leibniz award,
F.G.) for generous financial support. We thank C. Schlep-
phorst, Dr. D. Zhao, Dr. L. Candish, and Dr. M. van Gemme-
ren for helpful discussions. We also thank Dr. C. G. Daniliuc
for the X-ray crystallographic analysis.
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
REFERENCES
(1) Selected reviews: (a) Herrmann, W. A. Angew. Chem., Int. Ed.
2002, 41, 1290. (b) Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed.
2008, 47, 3122. (c) Díez-González, S.; Marion, N.; Nolan, S. P. Chem.
Rev. 2009, 109, 3612. (d) Dröge, T.; Glorius, F. Angew. Chem., Int. Ed.
2010, 49, 6940. (e) Gaillard, S.; Cazin, C. S. J.; Nolan, S. P. Acc. Chem.
Res. 2012, 45, 778. (f) Valente, C.; Çalimsiz, S.; Hoi, K. H.; Mallik, D.;
Sayah, M.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 3314. (g)
Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Nature 2014,
510, 485.
(2) Herrmann, W. A.; Goossen, L. T.; Köcher, C.; Artus, G. R. J.
Angew. Chem., Int. Ed. 1996, 35, 2805.
(3) (a) Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14,
951. (b) César, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev.
2004, 33, 619. (c) Gade, L. H.; Bellemin-Laponnaz, S. Coord. Chem.
Rev. 2007, 251, 718. (d) Wang, F.; Liu, L.-j.; Wang, W.; Li, S.; Shi, M.
Coord. Chem. Rev. 2012, 256, 804. (e) Zhao, D.; Candish, L.; Paul, D.;
Glorius, F. ACS Catal. 2016, 6, 5978.
(4) For selected examples, see: (a) Seiders, T. J.; Ward, D. W.;
Grubbs, R. H. Org. Lett. 2001, 3, 3225. (b) Lee, S.; Hartwig, J. F. J. Org.
Chem. 2001, 66, 3402. (c) Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.;
Andrus, M. B. Angew. Chem., Int. Ed. 2003, 42, 5871. (d) Alexakis, A.;
Winn, C. L.; Guillen, F.; Pytkowicz, J.; Roland, S.; Mangeney, P. Adv.
Synth. Catal. 2003, 345, 345. (e) Kündig, E. P.; Seidel, T. M.; Jia, Y.-X.;
Bernardinelli, G. Angew. Chem., Int. Ed. 2007, 46, 8484. (f)
Chaulagain, M. R.; Sormunen, G. J.; Montgomery, J. J. Am. Chem. Soc.
2007, 129, 9568. (g) Würtz, S.; Lohre, C.; Fröhlich, R.; Bergander, K.;
Glorius, F. J. Am. Chem. Soc. 2009, 131, 8344. (h) Liu, L.; Ishida, N.;
Ashida, S.; Murakami, M. Org. Lett. 2011, 13, 1666. (i) Hartung, J.;
Grubbs, R. H. J. Am. Chem. Soc. 2013, 135, 10183. (j) Dasgupta, A.;
Ramkumar, V.; Sankararaman, S. RSC Adv. 2015, 5, 21558.
(5) Powell, M. T.; Hou, D.-R.; Perry, M. C.; Cui, X.; Burgess, K. J.
Am. Chem. Soc. 2001, 123, 8878.
(6) For selected examples, see: (a) Duan, W.-L.; Shi, M.; Rong, G.-
B. Chem. Commun. 2003, 2916. (b) Bonnet, L. G.; Douthwaite, R. E.;
Hodgson, R. Organometallics 2003, 22, 4384. (c) Perry, M. C.; Cui, X.;
Powell, M. T.; Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Am. Chem.
Soc. 2003, 125, 113. (d) César,V.; Bellemin-Laponnaz, S.; Gade, L. H.
Organometallics 2002, 21, 5204. (e) César, V.; Bellemin-Laponnaz, S.;
Gade, L. H. Angew. Chem., Int Ed. 2004, 43, 1014. (f) Nanchen, S.;
Pfaltz, A. Chem. − Eur. J. 2006, 12, 4550. (g) Schumacher, A.;
Bernasconi, M.; Pfaltz, A. Angew. Chem., Int. Ed. 2013, 52, 7422. (h)
Wan, K. Y.; Lough, A. J.; Morris, R. H. Organometallics 2016, 35, 1604.
(i) Van Veldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H.
J. Am. Chem. Soc. 2002, 124, 4954. (j) Kacprzynski, M. A.; May, T. L.;
Kazane, S. A.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2007, 46, 4554.
(k) Bappert, E.; Helmchen, G. Synlett 2004, 10, 1789. (l) Sakaguchi, S.;
Yoo, K. S.; O’Neill, J.; Lee, J. H.; Stewart, T.; Jung, K. W. Angew.
Chem., Int. Ed. 2008, 47, 9326. (m) Seo, H.; Park, H.-J.; Kim, B. Y.;
Lee, J. H.; Son, S. U.; Chung, Y. K. Organometallics 2003, 22, 618. (n)
(19) Anderson, N. G. in Practical Process Research and Develop-
ment, second Ed. Elsevier: Oxford, 2012, p. 98.
(20) (a) Rieche, A.; Gross, H.; Höft, E. Chem. Ber. 1960, 93, 88. (b)
Lenz, C. A.; Rychlik, M. Tetrahedron Lett. 2013, 54, 883.
(21) (a) Bal, B. S.; Childers Jr., W. E.; Pinnick, H. W. Tetrahedron
1981, 37, 2091. (b) Kanamori, D.; Okamura, T.-a.; Yamamoto, H.;
Shimizu, S.; Tsujimoto,Y.; Ueyama, N. Bull. Chem. Soc. Jpn. 2004, 77,
2057.
(22) Gabriele, B.; Attya, M.; Fazio, A.; Di Donna, L.; Plastina, P.;
Sindona, G. Synthesis 2009, 1815.
ACS Paragon Plus Environment