-
1
-
-
33644554591
-
-
Dyker, G., Ed.; Wiley-VCH: Weinheim
-
Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. In Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, 2005; Vol. 1, p 187.
-
(2005)
Handbook of C-H Transformations
, vol.1
, pp. 187
-
-
Wiedemann, S.H.1
Bergman, R.G.2
Ellman, J.A.3
-
3
-
-
0036589261
-
-
(b) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
-
(2002)
Chem. Rev.
, vol.102
, pp. 1731
-
-
Ritleng, V.1
Sirlin, C.2
Pfeffer, M.3
-
4
-
-
0002675313
-
-
Murai, S., Ed.; Freund Pub. House: London
-
(c) Kakiuchi, F.; Murai, S. In Activation of Unreactive Bonds in Organic Synthesis; Murai, S., Ed.; Freund Pub. House: London, 1999; Vol. 3, p 47.
-
(1999)
Activation of Unreactive Bonds in Organic Synthesis
, vol.3
, pp. 47
-
-
Kakiuchi, F.1
Murai, S.2
-
5
-
-
0027913099
-
-
Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
-
(1993)
Nature
, vol.366
, pp. 529
-
-
Murai, S.1
Kakiuchi, F.2
Sekine, S.3
Tanaka, Y.4
Kamatani, A.5
Sonoda, M.6
Chatani, N.7
-
6
-
-
0001818455
-
-
For a discussion of a cyclometalation mechanism involving direct oxidative addition, see: Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62.
-
(1995)
Bull. Chem. Soc. Jpn.
, vol.68
, pp. 62
-
-
Kakiuchi, F.1
Sekine, S.2
Tanaka, Y.3
Kamatani, A.4
Sonoda, M.5
Chatani, N.6
Murai, S.7
-
7
-
-
0032501467
-
-
0, followed by α-elimination, see: (a) Matsubara, T.; Koga, N.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 12692.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 12692
-
-
Matsubara, T.1
Koga, N.2
Musaev, D.G.3
Morokuma, K.4
-
8
-
-
0033703742
-
-
(b) Matsubara, T.; Koga, N.; Musaev, D. G.; Morokuma, K. Organometallics 2000, 19, 2318.
-
(2000)
Organometallics
, vol.19
, pp. 2318
-
-
Matsubara, T.1
Koga, N.2
Musaev, D.G.3
Morokuma, K.4
-
11
-
-
0000575557
-
-
Jordan, R. F.; Taylor, D. F.; Baenziger, N. C. Organometallics 1990, 9, 1546.
-
(1990)
Organometallics
, vol.9
, pp. 1546
-
-
Jordan, R.F.1
Taylor, D.F.2
Baenziger, N.C.3
-
12
-
-
0001687709
-
-
Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; Labounty, L.; Chou, L.; Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 5888
-
-
Moore, E.J.1
Pretzer, W.R.2
O'Connell, T.J.3
Harris, J.4
Labounty, L.5
Chou, L.6
Grimmer, S.S.7
-
13
-
-
0000171099
-
-
(a) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 493
-
-
Chatani, N.1
Fukuyama, T.2
Kakiuchi, F.3
Murai, S.4
-
14
-
-
0032508875
-
-
(b) Fukuyama, T.; Chatani, N.; Tatsumi, J.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1998, 120, 11522.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 11522
-
-
Fukuyama, T.1
Chatani, N.2
Tatsumi, J.3
Kakiuchi, F.4
Murai, S.5
-
15
-
-
0034733109
-
-
(c) Chatani, N.; Fukuyama, T.; Tatamidani, H.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 4039.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 4039
-
-
Chatani, N.1
Fukuyama, T.2
Tatamidani, H.3
Kakiuchi, F.4
Murai, S.5
-
16
-
-
0035825161
-
-
(d) Szewczyk, J. W.; Zuckerman, R. L.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2001, 40, 216.
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 216
-
-
Szewczyk, J.W.1
Zuckerman, R.L.2
Bergman, R.G.3
Ellman, J.A.4
-
17
-
-
1342332903
-
-
(a) Youn, S. W.; Pastine, S. J.; Sames, D. Org. Lett. 2004, 6, 581.
-
(2004)
Org. Lett.
, vol.6
, pp. 581
-
-
Youn, S.W.1
Pastine, S.J.2
Sames, D.3
-
18
-
-
9144234212
-
-
(b) Pittard, K. A.; Lee, J. P.; Cundari, T. R.; Gunnoe, T. B.; Petersen, J. L. Organometallics 2004, 23, 5514.
-
(2004)
Organometallics
, vol.23
, pp. 5514
-
-
Pittard, K.A.1
Lee, J.P.2
Cundari, T.R.3
Gunnoe, T.B.4
Petersen, J.L.5
-
19
-
-
1642281558
-
-
(a) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 3700
-
-
Liu, C.1
Han, X.2
Wang, X.3
Widenhoefer, R.A.4
-
21
-
-
4143129865
-
-
(c) Liu, C.; Han, X. Q.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 10493.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 10493
-
-
Liu, C.1
Han, X.Q.2
Wang, X.3
Widenhoefer, R.A.4
-
24
-
-
2542641534
-
-
Some oxidative protocols for the heterocycle/olefin couple have appeared recently: (a) DeBoef, B.; Pastine, S. J.; Sames, D. J. Am. Chem. Soc. 2004, 126, 6556.
-
(2004)
Am. Chem. Soc.
, vol.126
, pp. 6556
-
-
DeBoef, B.1
Pastine, S.J.2
Sames, D.J.3
-
25
-
-
9144238852
-
-
(b) Yi, C. S.; Yun, S. Y.; Guzei, I. A. Organometallics 2004, 23, 5392.
-
(2004)
Organometallics
, vol.23
, pp. 5392
-
-
Yi, C.S.1
Yun, S.Y.2
Guzei, I.A.3
-
28
-
-
0034827123
-
-
(a) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 2685.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 2685
-
-
Tan, K.L.1
Bergman, R.G.2
Ellman, J.A.3
-
29
-
-
0037184456
-
-
(b) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 13964
-
-
Tan, K.L.1
Bergman, R.G.2
Ellman, J.A.3
-
30
-
-
0037012428
-
-
(c) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 3202.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 3202
-
-
Tan, K.L.1
Bergman, R.G.2
Ellman, J.A.3
-
31
-
-
0141630581
-
-
(d) Tan, K. L.; Vasudevan, A.; Bergman, R. G.; Ellman, J. A.; Souers, A. J. Org. Lett. 2003, 5, 2131.
-
(2003)
Org. Lett.
, vol.5
, pp. 2131
-
-
Tan, K.L.1
Vasudevan, A.2
Bergman, R.G.3
Ellman, J.A.4
Souers, A.J.5
-
32
-
-
5444275842
-
-
(e) Tan, K. L.; Park, S.; Ellman, J. A.; Bergman, R. G. J. Org. Chem. 2004, 69, 7329.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 7329
-
-
Tan, K.L.1
Park, S.2
Ellman, J.A.3
Bergman, R.G.4
-
33
-
-
2542519356
-
-
Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 1685.
-
(2004)
Org. Lett.
, vol.6
, pp. 1685
-
-
Wiedemann, S.H.1
Bergman, R.G.2
Ellman, J.A.3
-
35
-
-
0346341139
-
-
For a previous synthesis of a 1-derived M-NHC complex, see: Basato, M.; Benetollo, F.; Facchin, G.; Michelin, R. A.; Mozzon, M.; Pugliese, S.; Sgarbossa, P.; Sbovata, S. M.; Tassan, A. J. Organomet. Chem. 2004, 689, 454.
-
(2004)
J. Organomet. Chem.
, vol.689
, pp. 454
-
-
Basato, M.1
Benetollo, F.2
Facchin, G.3
Michelin, R.A.4
Mozzon, M.5
Pugliese, S.6
Sgarbossa, P.7
Sbovata, S.M.8
Tassan, A.9
-
36
-
-
0742321839
-
-
Lewis, J. C.; Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 35.
-
(2004)
Org. Lett.
, vol.6
, pp. 35
-
-
Lewis, J.C.1
Wiedemann, S.H.2
Bergman, R.G.3
Ellman, J.A.4
-
38
-
-
0000615125
-
-
(a) Mendez, N. Q.; Seyler, J. W.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 2323.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 2323
-
-
Mendez, N.Q.1
Seyler, J.W.2
Arif, A.M.3
Gladysz, J.A.4
-
40
-
-
33644498947
-
-
note
-
While we have chosen to depict the metal center of 3 as square planar, we cannot rule out the presence of one weakly bound inner-sphere solvent ligand.
-
-
-
-
41
-
-
0000647798
-
-
Yao, W. B.; Eisenstein, O.; Crabtree, R. H. Inorg. Chim. Acta 1997, 254, 105.
-
(1997)
Inorg. Chim. Acta
, vol.254
, pp. 105
-
-
Yao, W.B.1
Eisenstein, O.2
Crabtree, R.H.3
-
42
-
-
33644512867
-
-
Pre-agostic interactions have been identified as intermediates preceding C-H oxidative addition. The question of whether the C8-H bond of 3 can undergo metal-insertion is beyond the scope of this report. For a discussion of this rare type of interaction in a related system, see: Lewis, J. C.; Wu, J.; Bergman, R. G.; Ellman, J. A. Organometallics 2005, 24, 5737.
-
(2005)
Organometallics
, vol.24
, pp. 5737
-
-
Lewis, J.C.1
Wu, J.2
Bergman, R.G.3
Ellman, J.A.4
-
46
-
-
0000212288
-
-
2RhCl has been implicated in the decomposition of this complex: Hietkamp, S.; Stufkens, D. J.; Vrieze, K. J. Organomet. Chem. 1978, 152, 347.
-
(1978)
J. Organomet. Chem.
, vol.152
, pp. 347
-
-
Hietkamp, S.1
Stufkens, D.J.2
Vrieze, K.3
-
47
-
-
33644501579
-
-
note
-
2H NMR.
-
-
-
-
48
-
-
33644526366
-
-
note
-
Another scenario that is consistent with the observed data is a large extent of crossover in conjunction with a large kinetic isotope effect. This interpretation is invalidated by the small measured kinetic isotope effect (vide infra).
-
-
-
-
49
-
-
33644541906
-
-
note
-
3).
-
-
-
-
52
-
-
33644536516
-
-
note
-
2RhCl, see ref 30a.
-
-
-
-
53
-
-
33644524188
-
-
note
-
2RhCl.
-
-
-
-
54
-
-
33644552214
-
-
note
-
The omission of more complicated [Rh] equilibria was not found to affect data fitting.
-
-
-
-
55
-
-
33644524806
-
-
note
-
3RhCl (ref 30b).
-
-
-
-
56
-
-
1842502863
-
-
For treatments of uncatalyzed and proton-catalyzed 1,2-hydrogen shifts at imidazol-2-yl carbenes, see: (a) Amyes, T. L.; Diver, S. T.; Richard, J. P.; Rivas, F. M.; Toth, K. J. Am. Chem. Soc. 2004, 126, 4366.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 4366
-
-
Amyes, T.L.1
Diver, S.T.2
Richard, J.P.3
Rivas, F.M.4
Toth, K.5
-
57
-
-
0002138516
-
-
(b) Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
-
(2000)
Chem. Rev.
, vol.100
, pp. 39
-
-
Bourissou, D.1
Guerret, O.2
Gabbai, F.P.3
Bertrand, G.4
-
58
-
-
84961978582
-
-
36b see: (a) Hawkes, K. J.; McGuinness, D. S.; Cavell, K. J.; Yates, B. F. Dalton Trans. 2004, 2505.
-
(2004)
Dalton Trans.
, pp. 2505
-
-
Hawkes, K.J.1
McGuinness, D.S.2
Cavell, K.J.3
Yates, B.F.4
-
59
-
-
28044454126
-
-
(b) Appelhans, L. N.; Zuccaccia, D.; Kovacevic, A.; Chianese, A. R.; Miecznikowski, J. R.; Macchioni, A.; Clot, E.; Eisenstein, O.; Crabtree, R. H. J. Am. Chem. Soc. 2005, 127, 16299.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 16299
-
-
Appelhans, L.N.1
Zuccaccia, D.2
Kovacevic, A.3
Chianese, A.R.4
Miecznikowski, J.R.5
Macchioni, A.6
Clot, E.7
Eisenstein, O.8
Crabtree, R.H.9
-
60
-
-
33644537470
-
-
note
-
For the sake of simplicity, no inner-sphere solvent molecules were included in our models. In a related system, reaction coordinates calculated with inner sphere solvent did not differ significantly from coordinates lacking solvation (ref 36a).
-
-
-
-
61
-
-
0001050367
-
-
Crabtree, R. H.; Holt, E. M.; Lavin, M.; Morehouse, S. M. Inorg. Chem. 1985, 24, 1986.
-
(1985)
Inorg. Chem.
, vol.24
, pp. 1986
-
-
Crabtree, R.H.1
Holt, E.M.2
Lavin, M.3
Morehouse, S.M.4
-
62
-
-
33644544841
-
-
note
-
1H NMR resonances in the hydride region.
-
-
-
-
63
-
-
33644552884
-
-
note
-
2RhCl (-10.4 cal/mol·K, ref 36a).
-
-
-
-
64
-
-
6044253710
-
-
An instance of ortho-directed transition metal-mediated C-H activation that is not chelation-assisted has been recently reported: Zhang, X. W.; Kanzelberger, M.; Emge, T. J.; Goldman, A. S. J. Am. Chem. Soc. 2004, 126, 13192.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 13192
-
-
Zhang, X.W.1
Kanzelberger, M.2
Emge, T.J.3
Goldman, A.S.4
-
65
-
-
33644499269
-
-
note
-
Maintaining N-coordination during C-H oxidative addition of an N-heterocycle would lead to a strained three-membered chelate ring. This type of coordination is known exclusively for early metals. See ref 8 and references therein.
-
-
-
-
66
-
-
4544294920
-
-
Clement, N. D.; Cavell, K. J. Angew. Chem., Int. Ed. 2004, 43, 3845.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 3845
-
-
Clement, N.D.1
Cavell, K.J.2
-
67
-
-
2942545879
-
-
Clement, N. D.; Cavell, K. J.; Jones, C.; Elsevier, C. J. Angew. Chem., Int. Ed. 2004, 43, 1277.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 1277
-
-
Clement, N.D.1
Cavell, K.J.2
Jones, C.3
Elsevier, C.J.4
-
69
-
-
0037019663
-
-
(a) Grundemann, S.; Kovacevic, A.; Albrecht, M.; Faller, J. W.; Crabtree, R. H. J. Am. Chem. Soc. 2002, 124, 10473.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 10473
-
-
Grundemann, S.1
Kovacevic, A.2
Albrecht, M.3
Faller, J.W.4
Crabtree, R.H.5
-
70
-
-
1942456891
-
-
(b) Lebel, H.; Janes, M. K.; Charette, A. B.; Nolan, S. P. J. Am. Chem. Soc. 2004, 126, 5046.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 5046
-
-
Lebel, H.1
Janes, M.K.2
Charette, A.B.3
Nolan, S.P.4
-
71
-
-
33644516087
-
-
Reference 36b
-
(c) Reference 36b.
-
-
-
-
72
-
-
3242657915
-
-
(a) Lavallo, V.; Mafhouz, J.; Canac, Y.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. J. Am. Chem. Soc. 2004, 126, 8670.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 8670
-
-
Lavallo, V.1
Mafhouz, J.2
Canac, Y.3
Donnadieu, B.4
Schoeller, W.W.5
Bertrand, G.6
-
73
-
-
24944490141
-
-
(b) Lavallo, V.; Canac, Y.; Prasang, C.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2005, 44, 5705.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 5705
-
-
Lavallo, V.1
Canac, Y.2
Prasang, C.3
Donnadieu, B.4
Bertrand, G.5
-
74
-
-
33644546136
-
-
note
-
We have once observed functionalization at such a site in the case of the purine (ref 15b).
-
-
-
-
75
-
-
2442591069
-
-
Efficient, versatile Rh-catalyzed hydroiminoacylation is possible when the imine N-substituent is a metal-coordinating group (2-pyridyl). See: Jun, C. H.; Lee, J. H. Pure Appl. Chem. 2004, 76, 577.
-
(2004)
Pure Appl. Chem.
, vol.76
, pp. 577
-
-
Jun, C.H.1
Lee, J.H.2
-
76
-
-
0002263988
-
-
Alaimo, P. J.; Peters, D. W.; Arnold, J.; Bergman, R. G. J. Chem. Educ. 2001, 78, 64.
-
(2001)
J. Chem. Educ.
, vol.78
, pp. 64
-
-
Alaimo, P.J.1
Peters, D.W.2
Arnold, J.3
Bergman, R.G.4
-
79
-
-
0742321839
-
-
The 3,4-dihydroquinazoline was prepared according to a literature procedure: Lewis, J. C.; Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 35.
-
(2004)
Org. Lett.
, vol.6
, pp. 35
-
-
Lewis, J.C.1
Wiedemann, S.H.2
Bergman, R.G.3
Ellman, J.A.4
-
81
-
-
0037178121
-
-
Klapars, A.; Huang, X. H.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 7421
-
-
Klapars, A.1
Huang, X.H.2
Buchwald, S.L.3
-
82
-
-
0141852248
-
-
Analytical data and a synthetic protocol have been reported for (2-bromobenzyl)-methyl-amine: Philippe, N.; Denivet, F.; Vasse, J.-L.; Santos, J. S. O.; Levacher, V.; Dupas, G. Tetrahedron 2003, 59, 8049.
-
(2003)
Tetrahedron
, vol.59
, pp. 8049
-
-
Philippe, N.1
Denivet, F.2
Vasse, J.-L.3
Santos, J.S.O.4
Levacher, V.5
Dupas, G.6
-
84
-
-
33644523194
-
-
note
-
Prepared according to the procedure for 4.
-
-
-
-
86
-
-
0000216001
-
-
(b) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
-
(1980)
Can. J. Phys.
, vol.58
, pp. 1200
-
-
Vosko, S.H.1
Wilk, L.2
Nusair, M.3
-
87
-
-
0345491105
-
-
(c) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
-
(1988)
Phys. Rev. B
, vol.37
, pp. 785
-
-
Lee, C.T.1
Yang, W.T.2
Parr, R.G.3
-
88
-
-
26844534384
-
-
(d) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
-
(1980)
J. Chem. Phys.
, vol.72
, pp. 650
-
-
Krishnan, R.1
Binkley, J.S.2
Seeger, R.3
Pople, J.A.4
-
89
-
-
0007718740
-
-
Schrodinger, Inc.: Portland, OR
-
Jaguar 4.0, release 23; Schrodinger, Inc.: Portland, OR, 1998.
-
(1998)
Jaguar 4.0, Release 23
-
-
-
90
-
-
36549091139
-
-
Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265.
-
(1984)
J. Chem. Phys.
, vol.80
, pp. 3265
-
-
Frisch, M.J.1
Pople, J.A.2
Binkley, J.S.3
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