-
1
-
-
1542763298
-
-
For reviews on catalytic olefin metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452.
-
(1995)
Acc. Chem. Res.
, vol.28
, pp. 446-452
-
-
Grubbs, R.H.1
Miller, S.J.2
Fu, G.C.3
-
3
-
-
0030771019
-
-
(c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
-
(1997)
Angew. Chem., Int. Ed. Engl.
, vol.36
, pp. 2036-2056
-
-
Schuster, M.1
Blechert, S.2
-
15
-
-
0142023994
-
-
(o) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 4592-4633
-
-
Schrock, R.R.1
Hoveyda, A.H.2
-
16
-
-
1642531708
-
-
Buchmeiser, M. R., Ed.; Wiley-VCH: Weinheim, Germany
-
For brief overviews regarding supported olefin metathesis catalysts, see: (a) Kingsbury, J. S.; Hoveyda, A. H. In Polymeric Materials in Organic Synthesis and Catalysis; Buchmeiser, M. R., Ed.; Wiley-VCH: Weinheim, Germany, 2003; pp 467-502.
-
(2003)
Polymeric Materials in Organic Synthesis and Catalysis
, pp. 467-502
-
-
Kingsbury, J.S.1
Hoveyda, A.H.2
-
17
-
-
1642462100
-
-
(b) Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biol. Chem. 2004, 2, 8-23.
-
(2004)
Org. Biol. Chem.
, vol.2
, pp. 8-23
-
-
Hoveyda, A.H.1
Gillingham, D.G.2
Van Veldhuizen, J.J.3
Kataoka, O.4
Garber, S.B.5
Kingsbury, J.S.6
Harrity, J.P.A.7
-
18
-
-
0030893870
-
-
(a) Harrity, J. P. A.; Visser, M. S.; Gleason, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 1488-1489.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 1488-1489
-
-
Harrity, J.P.A.1
Visser, M.S.2
Gleason, J.D.3
Hoveyda, A.H.4
-
19
-
-
0032542683
-
-
(b) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343-2351.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 2343-2351
-
-
Harrity, J.P.A.1
La, D.S.2
Cefalo, D.R.3
Visser, M.S.4
Hoveyda, A.H.5
-
20
-
-
0033518572
-
-
(c) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 791-799
-
-
Kingsbury, J.S.1
Harrity, J.P.A.2
Bonitatebus, P.J.3
Hoveyda, A.H.4
-
21
-
-
0034734340
-
-
(d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 8168-8179
-
-
Garber, S.B.1
Kingsbury, J.S.2
Gray, B.L.3
Hoveyda, A.H.4
-
22
-
-
9144226393
-
-
For a most recent supported variant of 2, see: (e) Clavier, H.; Audic, N.; Mauduit, M.; Guillemin, J.-C. Chem. Commun. 2004, 2282-2283.
-
(2004)
Chem. Commun.
, pp. 2282-2283
-
-
Clavier, H.1
Audic, N.2
Mauduit, M.3
Guillemin, J.-C.4
-
23
-
-
0037042233
-
-
(a) Van Veldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954-4955.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 4954-4955
-
-
Van Veldhuizen, J.J.1
Garber, S.B.2
Kingsbury, J.S.3
Hoveyda, A.H.4
-
24
-
-
0141885397
-
-
(b) Van Veldhuizen, J. J.; Gillingham, D. G.; Garber, S. B.; Kataoka, O.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 12502-12508.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 12502-12508
-
-
Van Veldhuizen, J.J.1
Gillingham, D.G.2
Garber, S.B.3
Kataoka, O.4
Hoveyda, A.H.5
-
25
-
-
4644256135
-
-
(c) Gillingham, D. G.; Kataoka, O.; Garber, S. B.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 12288-12290.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 12288-12290
-
-
Gillingham, D.G.1
Kataoka, O.2
Garber, S.B.3
Hoveyda, A.H.4
-
26
-
-
18644377613
-
-
in press
-
See also: (d) Van Veldhuizen, J. J.; Campbell, J. E.; Giudici, R. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, in press.
-
(2005)
J. Am. Chem. Soc.
, vol.127
-
-
Van Veldhuizen, J.J.1
Campbell, J.E.2
Giudici, R.E.3
Hoveyda, A.H.4
-
27
-
-
0035807528
-
-
(e) Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225-3228.
-
(2001)
Org. Lett.
, vol.3
, pp. 3225-3228
-
-
Seiders, T.J.1
Ward, D.W.2
Grubbs, R.H.3
-
28
-
-
33746236970
-
-
(a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
-
(1995)
Angew. Chem., Int. Ed. Engl.
, vol.34
, pp. 2039-2041
-
-
Schwab, P.1
France, M.B.2
Ziller, J.W.3
Grubbs, R.H.4
-
29
-
-
0001855961
-
-
(b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 100-110
-
-
Schwab, P.1
Grubbs, R.H.2
Ziller, J.W.3
-
30
-
-
0033598258
-
-
Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
-
(1999)
Org. Lett.
, vol.1
, pp. 953-956
-
-
Scholl, M.1
Ding, S.2
Lee, C.W.3
Grubbs, R.H.4
-
31
-
-
2942631595
-
-
Grubbs, R. H., Ed.; VCH-Wiley: Weinheim, Germany, and references therein
-
Sanford, M. S.; Love, J. A. In Handbook of Olefin Metathesis; Grubbs, R. H., Ed.; VCH-Wiley: Weinheim, Germany, 2003; Vol. 1, pp 112-131, and references therein.
-
(2003)
Handbook of Olefin Metathesis
, vol.1
, pp. 112-131
-
-
Sanford, M.S.1
Love, J.A.2
-
32
-
-
85034336744
-
-
(a) Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 21, 4035-4037.
-
(2002)
Angew. Chem., Int. Ed.
, vol.21
, pp. 4035-4037
-
-
Love, J.A.1
Morgan, J.P.2
Trnka, T.M.3
Grubbs, R.H.4
-
33
-
-
0042020353
-
-
(b) Love, J. A.; Sanford, M. S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 10103-10109.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 10103-10109
-
-
Love, J.A.1
Sanford, M.S.2
Day, M.W.3
Grubbs, R.H.4
-
34
-
-
0000025162
-
-
For related reports on supported Ru-based complexes bearing monodentate carbenes used for olefin metathesis, where a similar release/return scenario is suggested, see: (a) Barrett, A. G. M.; Cramp, S. M.; Roberts, R. S. Org. Lett. 1999, 1, 1083-1086.
-
(1999)
Org. Lett.
, vol.1
, pp. 1083-1086
-
-
Barrett, A.G.M.1
Cramp, S.M.2
Roberts, R.S.3
-
35
-
-
0033521136
-
-
(b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 8657-8662
-
-
Ahmed, M.1
Barrett, A.G.M.2
Braddock, D.C.3
Cramp, S.M.4
Procopiou, P.A.5
-
36
-
-
0033931655
-
-
(c) Ahmed, M.; Arnauld, T.; Barrett, A. G. M.; Braddock, D. C.; Procopiou, P. A. Synlett 2000, 1007-1009.
-
(2000)
Synlett
, pp. 1007-1009
-
-
Ahmed, M.1
Arnauld, T.2
Barrett, A.G.M.3
Braddock, D.C.4
Procopiou, P.A.5
-
37
-
-
0035915174
-
-
Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2001, 40, 4251-4256.
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 4251-4256
-
-
Kingsbury, J.S.1
Garber, S.B.2
Giftos, J.M.3
Gray, B.L.4
Okamoto, M.M.5
Farrer, R.A.6
Fourkas, J.T.7
Hoveyda, A.H.8
-
38
-
-
16244396808
-
-
Grubbs, R. H., Ed.; VCH-Wiley: Wienheim, Germany
-
Nguyen, S. T.; Trnka, T. M. In Handbook of Olefin Metathesis; Grubbs, R. H., Ed.; VCH-Wiley: Wienheim, Germany, 2003; Vol. 1, p 77.
-
(2003)
Handbook of Olefin Metathesis
, vol.1
, pp. 77
-
-
Nguyen, S.T.1
Trnka, T.M.2
-
39
-
-
0037021049
-
-
For example, see: (a) Grela, K.; Harutyunyan, S.; Michrowska, A. Angew. Chem., Int. Ed. 2002, 41, 4038-4040.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 4038-4040
-
-
Grela, K.1
Harutyunyan, S.2
Michrowska, A.3
-
41
-
-
4644298316
-
-
(c) Bujok, R.; Bleniek, M.; Masnyk, M.; Michrowska, A.; Sarosiek, A.; Stepowska, H.; Arlt, D.; Grela, K. J. Org. Chem. 2004, 69, 6894-6896.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 6894-6896
-
-
Bujok, R.1
Bleniek, M.2
Masnyk, M.3
Michrowska, A.4
Sarosiek, A.5
Stepowska, H.6
Arlt, D.7
Grela, K.8
-
42
-
-
3342982883
-
-
(d) Michrowska, A.; Bujok, R.; Harutyunyan, S.; Sashuk, V.; Dolgonos, G.; Grela, K. J. Am. Chem. Soc. 2004, 126, 9318-9325.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 9318-9325
-
-
Michrowska, A.1
Bujok, R.2
Harutyunyan, S.3
Sashuk, V.4
Dolgonos, G.5
Grela, K.6
-
43
-
-
0037007937
-
-
(e) Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 2403-2405.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 2403-2405
-
-
Wakamatsu, H.1
Blechert, S.2
-
44
-
-
0042703435
-
-
(f) Zaja, M.; Connon, S. J.; Dunne, A. M.; Rivard, M.; Buschmann, N.; Jiricek, J.; Blechert, S. Tetrahedron 2003, 59, 6545-6558.
-
(2003)
Tetrahedron
, vol.59
, pp. 6545-6558
-
-
Zaja, M.1
Connon, S.J.2
Dunne, A.M.3
Rivard, M.4
Buschmann, N.5
Jiricek, J.6
Blechert, S.7
-
45
-
-
0346724630
-
-
(g) Krause, J. O.; Zarka, M. T.; Anders, U.; Weberskirch, R.; Nuyken, O.; Buchmeiser, M. R. Angew. Chem., Int. Ed. 2003, 42, 5965-5969.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 5965-5969
-
-
Krause, J.O.1
Zarka, M.T.2
Anders, U.3
Weberskirch, R.4
Nuyken, O.5
Buchmeiser, M.R.6
-
46
-
-
1242285552
-
-
(h) Krause, J. O.; Nuyken, O.; Wurst, K.; Buchmeiser, M. R. Chem. Eur. J. 2004, 10, 777-784.
-
(2004)
Chem. Eur. J.
, vol.10
, pp. 777-784
-
-
Krause, J.O.1
Nuyken, O.2
Wurst, K.3
Buchmeiser, M.R.4
-
47
-
-
0035800494
-
-
Another (not necessarily mechanistically related) observation indicating that alteration of the aryl substituents of an NHC ligand can have unexpected effects on the stability and reactivity of the derived Ru carbenes can be found in a recent synthesis of a related Ru carbene bearing 2,6-diisopropylphenyl substituents on the saturated NHC; a Ru hydride was isolated as a major byproduct. See: Furstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236-3253.
-
(2001)
Chem. Eur. J.
, vol.7
, pp. 3236-3253
-
-
Furstner, A.1
Ackermann, L.2
Gabor, B.3
Goddard, R.4
Lehmann, C.W.5
Mynott, R.6
Stelzer, F.7
Thiel, O.R.8
-
48
-
-
16244373114
-
-
note
-
See the Supporting Information for details.
-
-
-
-
50
-
-
16244421781
-
-
note
-
This compound is easily formed by ring-opening of commercially available cis-5-norbornene-endo-2,3-dicarboxylic anhydride with 2 equiv of the functionalized benzylic alcohol; for details, see ref 10.
-
-
-
-
51
-
-
16244405661
-
-
note
-
The value was calculated from the mass increase following functionalization of the glass surface.
-
-
-
-
52
-
-
16244423060
-
-
note
-
If stirring is allowed to proceed for a longer period, RCM proceeds to > 99% conversion for each catalyst. Reactions in Table 1 were stopped abruptly at 1 h simply by drawing the reaction mixture away from the catalyst pellet with a Pasteur pipet.
-
-
-
-
53
-
-
0030994105
-
-
(a) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887-3897.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 3887-3897
-
-
Dias, E.L.1
Nguyen, S.T.2
Grubbs, R.H.3
-
54
-
-
0035977649
-
-
(b) Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749-750.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 749-750
-
-
Sanford, M.S.1
Ulman, M.2
Grubbs, R.H.3
-
55
-
-
0034814443
-
-
(c) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543-6554.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 6543-6554
-
-
Sanford, M.S.1
Love, J.A.2
Grubbs, R.H.3
-
56
-
-
16244367826
-
-
Reference 8
-
(d) Reference 8.
-
-
-
-
57
-
-
16244403387
-
-
note
-
Mechanistic studies involving chiral Ru complex 3 (Chart 1) and its deuterated derivatives indicate that catalyst recovered in high yield (90%) after olefin metathesis represents unreleased Ru carbene. Thus, even with the less active chiral complex, bearing a bidentate and sterically bulky ligand, high activity can be achieved with ≤ 10% released carbene. See ref 4b.
-
-
-
-
58
-
-
0029860486
-
-
For early examples of RCM with solid-supported substrates, see: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606-9614.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 9606-9614
-
-
Miller, S.J.1
Blackwell, H.E.2
Grubbs, R.H.3
-
59
-
-
0029903708
-
-
(b) Schuster, M.; Pernerstorfer, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1979-1980.
-
(1996)
Angew. Chem., Int. Ed. Engl.
, vol.35
, pp. 1979-1980
-
-
Schuster, M.1
Pernerstorfer, J.2
Blechert, S.3
-
60
-
-
0030569374
-
-
(c) van Maarsveen, J. H.; den Hartog, J. A. J.; Engelen, V.; Finner, E.; Visser, G.; Kruse, C. G. Tetrahedron Lett. 1996, 37, 8249-8252.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 8249-8252
-
-
Van Maarsveen, J.H.1
Den Hartog, J.A.J.2
Engelen, V.3
Finner, E.4
Visser, G.5
Kruse, C.G.6
-
62
-
-
17744405184
-
-
(e) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourlomis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E. Nature 1997, 387, 268-272.
-
(1997)
Nature
, vol.387
, pp. 268-272
-
-
Nicolaou, K.C.1
Winssinger, N.2
Pastor, J.3
Ninkovic, S.4
Sarabia, F.5
He, Y.6
Vourlomis, D.7
Yang, Z.8
Li, T.9
Giannakakou, P.10
Hamel, E.11
|