Please do not adjust margins
Dalton Transactions
Page 9 of 11
DOI: 10.1039/C8DT03488E
Journal Name
ARTICLE
5029; c) M. Mastalir, E. Pittenauer, G. Allmaier and K. Kirchner, J.
Am. Chem. Soc., 2017, 139, 8812-8815; d) M. Mastalir, E.
Pittenauer, B. Stoger, G. Allmaier and K. Kirchner, Org. Lett., 2017,
19, 2178-2181.
8. a) C. Gunanathan, L. J. W. Shimon and D. Milstein, J. Am. Chem.
Soc., 2009, 131, 3146-+; b) C. Gunanathan, B. Gnanaprakasam, M.
A. Iron, L. J. W. Shimon and D. Milstein, J. Am. Chem. Soc., 2010,
132, 14763-14765.
9. a) E. Balaraman, B. Gnanaprakasam, L. J. W. Shimon and D.
Milstein, J. Am. Chem. Soc., 2010, 132, 16756-16758; b) E.
Balaraman, Y. Ben-David and D. Milstein, Angew. Chem. Int. Ed.,
2011, 50, 11702-11705.
Acknowledgements
The authors thank CNRS and Ecole polytechnique for financial
support. E. Dubois is acknowledged for the synthesis of 2-
(azidomethyl)-6-(hydroxymethyl)pyridine and S. Bourcier for
mass spectroscopy measurements.
Notes and references
10. S. Y. de Boer, T. J. Korstanje, S. R. La Rooij, R. Kox, J. N. H. Reek
and J. I. van der Vlugt, Organometallics, 2017, 36, 1541-1549.
11. a) J. Zhang, G. Leitus, Y. Ben-David and D. Milstein, Angew.
Chem. Int. Ed., 2006, 45, 1113-1115; b) C. Gunanathan, Y. Ben-David
and D. Milstein, Science, 2007, 317, 790-792; c) B. Gnanaprakasam,
E. Balaraman, Y. Ben-David and D. Milstein, Angew. Chem. Int. Ed.,
2011, 50, 12240-12244.
12. a) I. M. Marín and A. Auffrant, Eur. J. Inorg. Chem., 2018, 1634-
1644; b) T. P. A. Cao, S. Labouille, A. Auffrant, Y. Jean, X. F. Le Goff
and P. Le Floch, Daltosn Trans., 2011, 40, 10029-10037; c) T. P. A.
Cao, A. Buchard, X. F. Le Goff, A. Auffrant and C. K. Williams, Inorg.
Chem., 2012, 51, 2157-2169; d) T. P. A. Cao, G. Nocton, L. Ricard, X.
F. Le Goff and A. Auffrant, Angew.Chem. Int. Ed., 2014, 53, 1368-
1372; e) I. M. Marín, T. Cheisson, R. Singh-Chauhan, C. Herrero, M.
Cordier, C. Clavaguéra, G. Nocton and A. Auffrant, Chem. Eur. J.,
2017, 23, 17940-17953.
‡ Other precursors were used in order to avoid the presence of
triphenylphosphine in the coordination sphere but results were
disappointing. Reaction between LPh with [RuCl2(DMSO)] is slow
and leads to 2 isomers differing by the coordination of the
DMSO. Reaction with [RuCl2(nbd)]n led to different products
better results were obtained with [RuCl2(nbd)(py)2].
˧
dearomatized pyridine ring
LR* is used to label the resulting deprotonated ligand with a
1. a) T. Ikariya, K. Murata and R. Noyori, Org. Biomol. Chem., 2006,
4, 393-406; b) J. I. v. d. Vlugt and J. N. H. Reek, Angew. Chem. Int.
Ed., 2009, 48, 8832-8846; c) J. I. van der Vlugt, Eur. J. Inorg. Chem.,
2012, 363-375; d) J. R. Khusnutdinova and D. Milstein,
Angew.Chem. Int. Ed., 2015, 54, 12236-12273; e) H. Li, B. Zheng and
K.-W. Huang, Coord. Chem. Rev., 2015, 293-294, 116-138; f) R. H.
Morris, Acc. Chem. Res., 2015, 48, 1494-1502; g) T. Zell and D.
Milstein, Acc. Chem. Res., 2015, 48, 1979-1994.
2. a) T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikariya and R. Noyori, J.
Am. Chem. Soc., 1995, 117, 2675-2676; b) R. Noyori and S.
Hashiguchi, Acc. Chem. Res., 1997, 30, 97-102.
13. a) T. Cheisson, A. Auffrant and G. Nocton, Organometallics,
2015, 34, 5470-5478; b) T. Cheisson and A. Auffrant, Dalton Trans.,
2014, 43, 13399-13409; c) V. Cadierno, J. Diez, S. E. Garcia-Garrido,
S. Garcia-Granda and J. Gimeno, J. Chem. Soc., Dalton Trans., 2002,
1465-1472.
14. T. Cheisson and A. Auffrant, Dalton Trans., 2016, 45, 2069-2078.
15. M. W. P. Bebbington and D. Bourissou, Coord. Chem. Rev., 2009,
253, 1248-1261.
16. a) A. Sacco, G. Vasapollo, C. F. Nobile, A. Piergiovanni, M. A.
Pellinghelli and M. Lanfranchi, J. Organomet. Chem., 1988, 356,
397-409; b) M. Alvarez, N. Lugan and R. Mathieu, J. Chem. Soc.,
Dalton Trans., 1994, 2755-2760.
17. L. Yang, D. R. Powell and R. P. Houser, Dalton Trans., 2007, 955-
964.
3. a) P. Maire, T. Büttner, F. Breher, P. L. Floch and H. Grützmacher,
Angew. Chem. Int. Ed., 2005, 44, 6318-6323; b) K. Muñiz, Angew.
Chem. Int. Ed., 2005, 44, 6622-6627; c) C. P. Casey and H. Guan, J.
Am. Chem. Soc., 2007, 129, 5816-5817; d) T. Li, I. Bergner, F. N.
Haque, M. Zimmer-De Iuliis, D. Song and R. H. Morris,
Organometallics, 2007, 26, 5940-5949; e) M. Trincado, K. Kühlein
and H. Grützmacher, Chem. Eur. J., 2011, 17, 11905-11913; f) W.
Zuo, A. J. Lough, Y. F. Li and R. H. Morris, Science, 2013, 342, 1080-
1083; g) S. Werkmeister, K. Junge, B. Wendt, E. Alberico, H. Jiao, W.
Baumann, H. Junge, F. Gallou and M. Beller, Angew. Chem. Int. Ed.,
2014, 53, 8722-8726.
4. a) Y. Shvo, D. Czarkie, Y. Rahamim and D. F. Chodosh, J. Am.
Chem. Soc., 1986, 108, 7400-7402; b) R. Kawahara, K. i. Fujita and R.
Yamaguchi, Angew. Chem. Int. Ed., 2012, 51, 12790-12794; c) T.
Yan, B. L. Feringa and K. Barta, Nature Communications, 2014, 5,
5602; d) A. J. Rawlings, L. J. Diorazio and M. Wills, Org. Lett., 2015,
17, 1086-1089; e) C. M. Moore, B. Bark and N. K. Szymczak, ACS
Catal., 2016, 6, 1981-1990.
18. X. Tan, Y. Wang, Y. Liu, F. Wang, L. Shi, K.-H. Lee, Z. Lin, H. Lv and
X. Zhang, Org. Lett., 2015, 17, 454-457.
19. A. W. Addison, T. N. Rao, J. Reedijk, J. van Rijn and G. C.
Verschoor, J. Chem. Soc., Dalton Trans., 1984, 1349-1356.
20. a) C. Y. Liu, D. Y. Chen, M. C. Cheng, S. M. Peng and S. T. Liu,
Organometallics, 1995, 14, 1983-1991; b) C. Y. Liu, D. Y. Chen, G. H.
Lee, S. M. Peng and S. T. Liu, Organometallics, 1996, 15, 1055-1061.
21. S. Chakraborty, U. Gellrich, Y. Diskin-Posner, G. Leitus, L. Avram
and D. Milstein, Angew. Chem. Int. Ed., 2017, 56, 4229-4233.
22. D. Aguilar, R. Bielsa, T. Soler and E. P. Urriolabeitia,
Organometallics, 2011, 30, 642-648.
23. a) M. A. Leeson, B. K. Nicholson and M. R. Olsen, J. Organomet.
Chem., 1999, 579, 243-251; b) K. T. K. Chan, L. P. Spencer, J. D.
Masuda, J. S. J. McCahill, P. Wei and D. W. Stephan,
Organometallics, 2004, 23, 381-390; c) D. Aguilar, R. Bielsa, M.
Contel, A. Lledos, R. Navarro, T. Soler and E. P. Urriolabeitia,
Organometallics, 2008, 27, 2929-2936; d) E. Martinez-Arripe, F.
Jean-Baptiste-dit-Dominique, A. Auffrant, X. F. Le Goff, J. Thuilliez
and F. Nief, Organometallics, 2012, 31, 4854-4861; e) K. R. D.
Johnson and P. G. Hayes, Chem. Soc. Rev., 2013, 42, 1947-1960; f)
5. C. Gunanathan and D. Milstein, Chem. Rev., 2014, 114, 12024-
12087.
6. a) H. Salem, L. J. W. Shimon, Y. Diskin-Posner, G. Leitus, Y. Ben-
David and D. Milstein, Organometallics, 2009, 28, 4791-4806; b) S.
Kundu, W. W. Brennessel and W. D. Jones, Inorg. Chem., 2011, 50,
9443-9453; c) G. M. Adams, F. M. Chadwick, S. D. Pike and A. S.
Weller, Dalton Trans., 2015, 44, 6340-6342; d) D. W. Shaffer, I.
Bhowmick, A. L. Rheingold, C. Tsay, B. N. Livesay, M. P. Shores and J.
Y. Yang, Dalton Trans., 2016, 45, 17910-17917.
7. a) M. Mastalir, M. Glatz, N. Gorgas, B. Stoger, E. Pittenauer, G.
Allmaier, L. F. Veiros and K. Kirchner, Chem. Eur. J., 2016, 22, 12316-
12320; b) F. Bertini, M. Glatz, N. Gorgas, B. Stoger, M. Peruzzini, L.
F. Veiros, K. Kirchner and L. Gonsalvi, Chem. Sci., 2017, 8, 5024-
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 9
Please do not adjust margins