Journal of the American Chemical Society
Page 10 of 12
1
2
3
4
5
6
7
8
9
MacRaild, C. A.; Jackson, W. R.; Norton, R. S.; Robinson, A. J.
Chem. Commun. 2016, 52, 4446ꢀ49.
11 Lehman Jr, S. E.; Schwendeman, J. E.; O'Donnell, P. M.; Wagener,
Present Addresses
†School of Chemistry, Cardiff University, Main Building, Park
Place, Cardiff CF10 3AT, United Kingdom.
K. B. Inorg. Chim. Acta 2003, 345, 190ꢀ98.
Pancrazi, A.; Nolan, S. P.; Prunet, J. J. Organomet. Chem. 2002, 643,
247ꢀ52. Fokou, P. A.; Meier, M. A. R. Macromol. Rapid
Bourgeois,
D.;
Author Contributions
¶These authors contributed equally.
Commun. 2010, 31, 368ꢀ73. Kinderman, S. S.; van Maarseveen, J.
H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. Org. Lett. 2001, 3,
2045ꢀ48.
Schmidt, B. Eur. J. Org. Chem. 2004, 1865ꢀ80.
ACKNOWLEDGMENT
12 Hong, S. H.; Sanders, D. P.; Lee, C. W.; Grubbs, R. H. J. Am. Chem.
Soc. 2005, 127, 17160ꢀ61.
13 Donohoe, T. J.; O'Riordan, T. J. C.; Rosa, C. P. Angew. Chem. Int.
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
The authors gratefully acknowledge the Research Council of
Norway (RCN) for financial support via the FORNY2020 (grant
number 203379 and 239288), GASSMAKS (208335), and
FRINATEK (262370) programs and for CPU and storage reꢀ
sources granted through the NOTUR (NN2506K) and
NORSTORE (NS2506K) supercomputing programs. J. E. grateful
for the support of the German Academic Exchange Service
(DAAD) through a shortꢀterm scholarship for doctoral students.
W. S. acknowledges the University of Bergen for a doctoral felꢀ
lowship. Dr. Bjarte Holmelid is thanked for assistance with the
HRMS (DART) analyses. We are grateful to the Swissꢀ
Norwegian beamlines at the ESRF, Grenoble, France and to Dr.
D. Chernyshov for assistance on beamline BM1A.
Ed. 2009, 48, 1014ꢀ17.
Chem. Rev. 2009, 109, 3817ꢀ58.
Alcaide, B.; Almendros, P.; Luna, A.
Arisawa, M.; Terada, Y.;
Nakagawa, M.; Nishida, A. Angew. Chem. 2002, 114, 4926ꢀ28.
Schmidt, B. Eur. J. Org. Chem. 2003, 2003, 816ꢀ19.
Schmidt, B. J. Org. Chem. 2004, 69, 7672ꢀ87.
Arisawa, M.; Terada, Y.; Takahashi, K.; Nakagawa, M.;
Nishida, A. Chem. Rec. 2007, 7, 238ꢀ53.
14 Hong, S. H.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2004, 126,
7414ꢀ15.
15 Higman, C. S.; Plais, L.; Fogg, D. E. ChemCatChem 2013, 5, 3548ꢀ
51.
16 Young, A.; Vincent, M. A.; Hillier, I. H.; Percy, J. M.; Tuttle, T.
Dalton Trans. 2014, 43, 8493ꢀ98.
17 Higman, C. S.; Lanterna, A. E.; Marin, M. L.; Scaiano, J. C.; Fogg, D.
E. ChemCatChem 2016, 8, 2446ꢀ49.
18 Courchay, F. C.; Sworen, J. C.; Ghiviriga, I.; Abboud, K. A.;
Wagener, K. B. Organometallics 2006, 25, 6074ꢀ86.
19 Mathew, J.; Koga, N.; Suresh, C. H. Organometallics 2008, 27, 4666ꢀ
70. Poater, A.; BahriꢀLaleh, N.; Cavallo, L. Chem. Commun. 2011,
REFERENCES
1
Grubbs, R. H.; Wenzel, A. G.; O'Leary, D. J.; Khosravi, E., Eds.
Handbook of metathesis; 2nd ed.; WileyꢀVCH: Weinheim, 2015; Vol.
1ꢀ3.
2
3
Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1,
953ꢀ56.
Gessler, S.; Randl, S.; Blechert, S. Tetrahedron Lett. 2000, 41, 9973ꢀ
76. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J.
Am. Chem. Soc. 2000, 122, 8168ꢀ79.
47, 6674ꢀ76.
Barbasiewicz, M.; Grela, K.; Cavallo, L. Chem. Eur. J. 2010, 16,
14354ꢀ64. Vehlow, K.; Gessler, S.; Blechert, S. Angew. Chem.
Poater, A.; Ragone, F.; Correa, A.; Szadkowska, A.;
Int. Ed. 2007, 46, 8082ꢀ85. Trnka, T. M.; Morgan, J. P.; Sanford, M.
S.; Wilhelm, T. E.; Scholl, M.; Choi, T. L.; Ding, S.; Day, M. W.;
Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 2546ꢀ58.
4
Farina, V.; Horváth, A. In Handbook of Metathesis; 2nd ed.; Grubbs,
R. H., Wenzel, A. G., O'Leary, D. J., Khosravi, E., Eds.; WileyꢀVCH:
20 Hong, S. H.; Chlenov, A.; Day, M. W.; Grubbs, R. H. Angew. Chem.
Int. Ed. 2007, 46, 5148ꢀ51.
21 Tsang, W. C. P.; Schrock, R. R.; Hoveyda, A. H. Organometallics
Weinheim, 2015; Vol. 2, pp 633ꢀ58.
Stoianova, D.; Johns, A.;
Pederson, R. In Handbook of Metathesis; 2nd ed.; Grubbs, R. H.,
Wenzel, A. G., O'Leary, D. J., Khosravi, E., Eds.; WileyꢀVCH:
Weinheim, 2015; Vol. 2, pp 699ꢀ726.
2001, 20, 5658ꢀ69.
Romero, P. E.; Piers, W. E. J. Am.
Chem. Soc. 2007, 129, 1698ꢀ704.
5
6
Higman, C. S.; Lummiss, J. A. M.; Fogg, D. E. Angew. Chem. Int. Ed.
2016, 55, 3552ꢀ65.
Dinger, M. B.; Mol, J. C. Adv. Synth. Catal. 2002, 344, 671ꢀ77.
Marx, V. M.; Sullivan, A. H.; Melaimi, M.; Virgil, S. C.;
Keitz, B. K.; Weinberger, D. S.; Bertrand, G.; Grubbs, R. H. 2015, -
22 van Rensburg, W. J.; Steynberg, P. J.; Meyer, W. H.; Kirk, M. M.;
Forman, G. S. J. Am. Chem. Soc. 2004, 126, 14332ꢀ33.
23 Schrodi, Y. In Handbook of Metathesis; Grubbs, R. H., Wenzel, A.
G., O'Leary, D. J., Khosravi, E., Eds.; WileyꢀVCH: Weinheim,, 2015;
Vol. 1, pp 323–42.
24 van Rensburg, W. J.; Steynberg, P. J.; Kirk, M. M.; Meyer, W. H.;
Forman, G. S. J. Organomet. Chem. 2006, 691, 5312ꢀ25.
25 Whereas the combination of sterically demanding alkenes and
alkylidenes may lead to substantial barriers to dissociation and
association of olefins (NuñezꢀZarur, F.; SolansꢀMonfort, X.;
54, ꢀ 1923.
W.; Stoianova, D.; Papazian, J.; Wei, W. H.; Mallari, A.; Schrodi, Y.;
Pederson, R. L. Top. Catal. 2012, 55, 518ꢀ23. Patel, J.;
Nickel, A.; Ung, T.; Mkrtumyan, G.; Uy, J.; Lee, C.
Mujcinovic, S.; Jackson, W. R.; Robinson, A. J.; Serelis, A. K.; Such,
C. Green Chem. 2006, 8, 450ꢀ54.
7
Maechling, S.; Zaja, M.; Blechert, S. Adv. Synth. Catal. 2005, 347,
RodrıguezꢀSantiago, L.; Sodupe, M. Organometallics 2012, 31,
́
1413ꢀ22.
Conrad, J. C.; Fogg, D. E. Curr. Org. Chem. 2006,
4203), the opposite is true for small alkylidenes, or alkylideneꢀfree
complexes, as found in the present work. See the SI for more
information. .
10, 185ꢀ202.
du Toit, J. I.; van der Gryp, P.; Loock, M. M.; Tole,
T. T.; Marx, S.; Jordaan, J. H. L.; Vosloo, H. C. M. Catal. Today
2016, 275, 191ꢀ200. Schrodi, Y.; Ung, T.; Vargas, A.;
26 Some of the present addition and dissociation reactions do not have
barriers on the PES above those defined by complete separation of the
two molecules and can be expected to proceed close to the diffusion
limit. The corresponding estimate of the Eyringꢀderived free energy
barrier of these addition reactions is 4.4 kcal molꢀ1. See the SI for
more information. .
27 Nelson, D. J.; Percy, J. M. Dalton Trans. 2014, 43, 4674ꢀ79.
28 Fomine, S.; Tlenkopatchev, M. A. Organometallics 2007, 26, 4491ꢀ
97. Sliwa, P.; Kurleto, K.; Handzlik, J.; Rogalski, S.; Zak, P.;
Wyrzykiewicz, B.; Pietraszuk, C. Organometallics 2016, 35, 621ꢀ28.
29 Hassam, M.; Taher, A.; Arnott, G. E.; Green, I. R.; van Otterlo, W. A.
Mkrtumyan, G.; Lee, C. W.; Champagne, T. M.; Pederson, R. L.;
Hong, S. H. Clean: Soil, Air, Water 2008, 36, 669ꢀ73.
Hagen, J. Industrial Catalysis: A Practical Approach; 2 ed.; Wileyꢀ
VCH, 2006.
8
9
Arisawa, M.; Nishida, A.; Nakagawa, M. J. Organomet. Chem. 2006,
691, 5109ꢀ21.
Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104,
2199ꢀ238.
Hoveyda, A. H.; Malcolmson, S. J.; Meek, S. J.;
Zhugralin, A. R. Angew. Chem. Int. Ed. 2010, 49, 34ꢀ44.
Meek,
S. J.; O'Brien, R. V.; Llaveria, J.; Schrock, R. R.; Hoveyda, A. H.
Nature 2011, 471, 461ꢀ66. Prunet, J. Eur. J. Org. Chem. 2011,
2011, 3634ꢀ47.
L. Chem. Rev. 2015, 115, 5462ꢀ569.
P. R.; Herbert, M. B.; Grubbs, R. H. J. Am. Chem. Soc. 2012, 134,
693ꢀ99. Occhipinti, G.; Hansen, F. R.; Törnroos, K. W.;
Jensen, V. R. J. Am. Chem. Soc. 2013, 135, 3331ꢀ34.
Keitz, B. K.; Endo, K.; Patel,
10 Chhabra, S.; Belgi, A.; Bartels, P.; van Lierop, B. J.; Robinson, S. D.;
Kompella, S. N.; Hung, A.; Callaghan, B. P.; Adams, D. J.; Robinson,
A. J.; Norton, R. S. J. Med. Chem. 2014, 57, 9933ꢀ44.
Gleeson, E. C.; Wang, Z. J.; Robinson, S. D.; Chhabra, S.;
ACS Paragon Plus Environment