-
2
-
-
0035969272
-
-
(a) Moreno-Manas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524-4528.
-
(2001)
Organometallics
, vol.20
, pp. 4524-4528
-
-
Moreno-Manas, M.1
Pleixats, R.2
Villarroya, S.3
-
4
-
-
0001127732
-
-
(c) Benhaddou, R.; Czernecki, S.; Ville, G.; Zegar, A. Organometallics 1988, 7, 2435-2439.
-
(1988)
Organometallics
, vol.7
, pp. 2435-2439
-
-
Benhaddou, R.1
Czernecki, S.2
Ville, G.3
Zegar, A.4
-
5
-
-
0342769612
-
-
(d) Zaw, K.; Lautens, M.; Henry, P. M. Organometallics 1983, 2, 197-199.
-
(1983)
Organometallics
, vol.2
, pp. 197-199
-
-
Zaw, K.1
Lautens, M.2
Henry, P.M.3
-
6
-
-
0001495283
-
-
(e) Tomioka, H.; Takai, K.; Oshina, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605-1608.
-
(1981)
Tetrahedron Lett.
, vol.22
, pp. 1605-1608
-
-
Tomioka, H.1
Takai, K.2
Oshina, K.3
Nozaki, H.4
-
7
-
-
0038106766
-
-
For a recent review on Pd-catalyzed oxidations of alcohols, see: Muzart, J. Tetrahedron 2003, 59, 5789-5816.
-
(2003)
Tetrahedron
, vol.59
, pp. 5789-5816
-
-
Muzart, J.1
-
8
-
-
0038308297
-
-
Nikiforova, A. V.; Moiseev, I. I.; Syrkin, Y. K. Zh. Obshch. Khim. 1964, 33, 3239-3242.
-
(1964)
Zh. Obshch. Khim.
, vol.33
, pp. 3239-3242
-
-
Nikiforova, A.V.1
Moiseev, I.I.2
Syrkin, Y.K.3
-
12
-
-
0038601681
-
-
This oxidative system has been extended to several transformations. For intramolecular cyclizations. heterocyclizations, and carbocylizations, see: (a) Toyota, M.; Sasaki, M.; Ihara, M. Org. Lett. 2003, 5, 1193-1195.
-
(2003)
Org. Lett.
, vol.5
, pp. 1193-1195
-
-
Toyota, M.1
Sasaki, M.2
Ihara, M.3
-
13
-
-
0037123673
-
-
(b) Toyota, M.; Rudyanto, M.; Ihara, M. J. Org. Chem. 2002, 67, 3374-3386.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 3374-3386
-
-
Toyota, M.1
Rudyanto, M.2
Ihara, M.3
-
15
-
-
0037771626
-
-
(d) Toyota, M.; Ilangovan, A.; Okamoto, R.; Masaki, T.; Arakawa, M.; Ihara, M. Org. Lett. 2002, 4, 4293-4296.
-
(2002)
Org. Lett.
, vol.4
, pp. 4293-4296
-
-
Toyota, M.1
Ilangovan, A.2
Okamoto, R.3
Masaki, T.4
Arakawa, M.5
Ihara, M.6
-
16
-
-
0034692385
-
-
(e) Toyota, M.; Odashima, T.; Wada, T.; Ihara, M. J. Am. Chem. Soc. 2000, 122, 9036-9037.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 9036-9037
-
-
Toyota, M.1
Odashima, T.2
Wada, T.3
Ihara, M.4
-
17
-
-
0034638730
-
-
(f) Toyota, M.; Rudyanto, M.; Ihara, M. Tetrahedron Lett. 2000, 41, 8929-8932.
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 8929-8932
-
-
Toyota, M.1
Rudyanto, M.2
Ihara, M.3
-
18
-
-
0034725823
-
-
(g) Toyota, M.; Wada, T.; Ihara, M. J. Org. Chem. 2000, 65, 4565-4570.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 4565-4570
-
-
Toyota, M.1
Wada, T.2
Ihara, M.3
-
19
-
-
0032572056
-
-
(h) Toyota, M.; Wada, T.; Fukumoto, K.; Ihara, M. J. Am. Chem. Soc. 1998, 720, 4916-4925.
-
(1998)
J. Am. Chem. Soc.
, vol.720
, pp. 4916-4925
-
-
Toyota, M.1
Wada, T.2
Fukumoto, K.3
Ihara, M.4
-
21
-
-
0037798563
-
-
(j) Rönn, M.; Andersson, P. G.; Bäckvall, J.-E. Tetrahedron Lett. 1997, 38, 3603-3606.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 3603-3606
-
-
Rönn, M.1
Andersson, P.G.2
Bäckvall, J.-E.3
-
22
-
-
0342738570
-
-
(k) Rönn, M.; Andersson, P. G.; Bäckvall, J.-E. Acta Chem. Scand. 1997, 51, 773-777.
-
(1997)
Acta Chem. Scand.
, vol.51
, pp. 773-777
-
-
Rönn, M.1
Andersson, P.G.2
Bäckvall, J.-E.3
-
23
-
-
0001338814
-
-
(l) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584-3585.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 3584-3585
-
-
Larock, R.C.1
Hightower, T.R.2
Hasvold, L.A.3
Peterson, K.P.4
-
24
-
-
0028832448
-
-
(m) Rönn, M.; Bäckvall, J.-E.; Andersson, P. G. Tetrahedron Lett. 1995, 36, 7749-7752.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 7749-7752
-
-
Rönn, M.1
Bäckvall, J.-E.2
Andersson, P.G.3
-
25
-
-
33748242802
-
-
(n) van Bentham, R. A. T. M.; Hiemstra, H.; van Leeuwen, P. W. N. M.; Geus, J. W.; Speckamp, W. N. Angew. Chem., Int. Ed. Engl. 1995, 34, 457-460.
-
(1995)
Angew. Chem., Int. Ed. Engl.
, vol.34
, pp. 457-460
-
-
Van Bentham, R.A.T.M.1
Hiemstra, H.2
Van Leeuwen, P.W.N.M.3
Geus, J.W.4
Speckamp, W.N.5
-
26
-
-
0028096866
-
-
(o) van Bentham, R. A. T. M.; Hiemstra, H.; Longarela, G. R.; Speckamp, W. N. Tetrahedron Lett. 1994, 35, 9281-9284.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 9281-9284
-
-
Van Bentham, R.A.T.M.1
Hiemstra, H.2
Longarela, G.R.3
Speckamp, W.N.4
-
27
-
-
37049077422
-
-
(p) van Bentham, R. A. T. M.; Hiemstra, H.; Michels, J. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1994, 357-359.
-
(1994)
J. Chem. Soc., Chem. Commun.
, pp. 357-359
-
-
Van Bentham, R.A.T.M.1
Hiemstra, H.2
Michels, J.J.3
Speckamp, W.N.4
-
29
-
-
0028899917
-
-
2 in DMSO, see: Larock, R. C.; Hightower, T. R.; Kraus, G. A.; Hahn, P.; Zheng, D. Tetrahedron Lett. 1995, 36, 2423-2426.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 2423-2426
-
-
Larock, R.C.1
Hightower, T.R.2
Kraus, G.A.3
Hahn, P.4
Zheng, D.5
-
31
-
-
0032886391
-
-
(a) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750-6755.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 6750-6755
-
-
Nishimura, T.1
Onoue, T.2
Ohe, K.3
Uemura, S.4
-
32
-
-
0032514514
-
-
(b) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011-6014.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 6011-6014
-
-
Nishimura, T.1
Onoue, T.2
Ohe, K.3
Uemura, S.4
-
33
-
-
1342302388
-
-
For a review, see: Nishimura, T.; Ohe, K.; Uemura, S. Synlett 2004, 2, 201-216.
-
(2004)
Synlett
, vol.2
, pp. 201-216
-
-
Nishimura, T.1
Ohe, K.2
Uemura, S.3
-
34
-
-
0000692217
-
-
For ring opening of hydroxycyclopropanes, see: Park, S.-B.; Cha, J. K. Org. Lett. 2000, 2, 147-149.
-
(2000)
Org. Lett.
, vol.2
, pp. 147-149
-
-
Park, S.-B.1
Cha, J.K.2
-
35
-
-
0037016260
-
-
For intramolecular oxidative amination, see: Fix, S. R.; Brice, J. L.; Stahl, S. S. Angew. Chem., Int. Ed. 2002, 41, 164-166.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 164-166
-
-
Fix, S.R.1
Brice, J.L.2
Stahl, S.S.3
-
36
-
-
0038034779
-
-
For a Wacker cyclization, see: Trend, R. N.; Ramtohul, E. M.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2003, 42, 2892-2895.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 2892-2895
-
-
Trend, R.N.1
Ramtohul, E.M.2
Ferreira, E.M.3
Stoltz, B.M.4
-
38
-
-
0037631809
-
-
(a) ten Brink, G.-J.; Arends, I. W. C. E.; Hoogenraad, M.; Verspui, G.; Sheldon, R. A. Adv. Synth. Catal. 2003, 345, 497-505.
-
(2003)
Adv. Synth. Catal.
, vol.345
, pp. 497-505
-
-
Ten Brink, G.-J.1
Arends, I.W.C.E.2
Hoogenraad, M.3
Verspui, G.4
Sheldon, R.A.5
-
39
-
-
0010472440
-
-
(b) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355-369.
-
(2002)
Adv. Synth. Catal.
, vol.344
, pp. 355-369
-
-
Ten Brink, G.-J.1
Arends, I.W.C.E.2
Sheldon, R.A.3
-
40
-
-
0036738419
-
-
(c) Sheldon, R. A.; Arends, I. W. C. E.; ten-Brink, G.-J.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774-781.
-
(2002)
Acc. Chem. Res.
, vol.35
, pp. 774-781
-
-
Sheldon, R.A.1
Arends, I.W.C.E.2
Ten-Brink, G.-J.3
Dijksman, A.4
-
41
-
-
0034051594
-
-
(d) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636-1639.
-
(2000)
Science
, vol.287
, pp. 1636-1639
-
-
Ten Brink, G.-J.1
Arends, I.W.C.E.2
Sheldon, R.A.3
-
43
-
-
1942503307
-
-
For a related catalyst, see: (b) Paavola, S.; Zetterberg, K.; Privalov, T.; Csöregh, I.; Moberg, C. Adv. Synth. Catal. 2004, 346, 237-244.
-
(2004)
Adv. Synth. Catal.
, vol.346
, pp. 237-244
-
-
Paavola, S.1
Zetterberg, K.2
Privalov, T.3
Csöregh, I.4
Moberg, C.5
-
44
-
-
0027940175
-
-
Heterogeneous and biphasic Pd catalyst systems have been reported to oxidize alcohols under air atmosphere; see: (a) Gómez-Bengoa, E.; Noheda, P.; Echavarren, A. M. Tetrahedron Lett. 1994, 35, 7097-7098.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 7097-7098
-
-
Gómez-Bengoa, E.1
Noheda, P.2
Echavarren, A.M.3
-
45
-
-
0028906761
-
-
(b) Aït-Mohand, S.; Hénin, F.; Muzart, J. Tetrahedron Lett. 1995, 36, 2473-2476.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 2473-2476
-
-
Aït-Mohand, S.1
Hénin, F.2
Muzart, J.3
-
47
-
-
0142214634
-
-
3 in oxidative amination, see: Timokhin, V. I.; Anastasi, N. R.; Stahl, Shannon S. J. Am. Chem. Soc. 2003, 125, 12996-12997.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 12996-12997
-
-
Timokhin, V.I.1
Anastasi, N.R.2
Stahl Shannon, S.3
-
48
-
-
0037028556
-
-
Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766-767.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 766-767
-
-
Steinhoff, B.A.1
Fix, S.R.2
Stahl, S.S.3
-
50
-
-
0141789726
-
-
2-catalyzed oxidative kinetic resolution of secondary alcohols, see: (a) Mandai, S. K.; Sigman, M. S. J. Org. Chem. 2003, 68, 7535-7537.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 7535-7537
-
-
Mandai, S.K.1
Sigman, M.S.2
-
52
-
-
0037125518
-
-
(c) Mueller, J. A., Jensen, D. R.; Sigman, M. S. J. Am. Chem. Soc. 2002, 124, 8202-8203.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 8202-8203
-
-
Mueller, J.A.1
Jensen, D.R.2
Sigman, M.S.3
-
53
-
-
0034823071
-
-
(d) Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475-7476.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 7475-7476
-
-
Jensen, D.R.1
Pugsley, J.S.2
Sigman, M.S.3
-
54
-
-
0034794864
-
-
Simultaneously and independently a related kinetic resolution was reported; see: (e) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725-7726.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 7725-7726
-
-
Ferreira, E.M.1
Stoltz, B.M.2
-
55
-
-
0038276940
-
-
(f) Bagdanoff, J. T.; Ferreira, E. M.; Stoltz, B. M. Org. Lett. 2003, 5, 835-837.
-
(2003)
Org. Lett.
, vol.5
, pp. 835-837
-
-
Bagdanoff, J.T.1
Ferreira, E.M.2
Stoltz, B.M.3
-
56
-
-
0346500606
-
-
(g) Bagdanoff, J. T.; Stoltz, B. M. Angew. Chem., Int. Ed. 2004, 43, 353-357.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 353-357
-
-
Bagdanoff, J.T.1
Stoltz, B.M.2
-
59
-
-
0042865830
-
-
Jensen, D. R.; Schultz, M. J.; Mueller, J. A.; Sigman, M. S. Angew. Chem., Int. Ed. 2003, 42, 3810-3813.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 3810-3813
-
-
Jensen, D.R.1
Schultz, M.J.2
Mueller, J.A.3
Sigman, M.S.4
-
60
-
-
3543115761
-
-
note
-
The sec-phenethyl alcohol concentration was decreased to 0.45 M, with the relative mole percentages of all other reagents remaining the same. These reactions were performed at 50 ± 0.1 °C in benzene. See the Supporting Information for details.
-
-
-
-
61
-
-
3543090030
-
-
note
-
2O).
-
-
-
-
63
-
-
0012297369
-
-
For a discussion on the magnitude of kinetic isotope effects, see: Westheimer, F. H. Chem. Rev. 1961, 61, 265-273.
-
(1961)
Chem. Rev.
, vol.61
, pp. 265-273
-
-
Westheimer, F.H.1
-
64
-
-
0346501634
-
-
Other scenarios have been reported where reactions with nonlinear transition states give high KIE values. The high KIE values were attributed to significant intermolecular force constants. For discussion of this concept, see: Motell, E. L.; Boone, A. W.; Fink, W. H. Tetrahedron 1978, 34, 1619-1626. Additionally, for discussion of proton-transfer reactions and KIE, see: O'Ferrall, R. A. M. In Proton-Transfer Reactions; Caldin, E. F., Gould, V., Eds.; Chapman & Hall: New York, 1975; Chapter 8.
-
(1978)
Tetrahedron
, vol.34
, pp. 1619-1626
-
-
Motell, E.L.1
Boone, A.W.2
Fink, W.H.3
-
65
-
-
0346501634
-
-
Caldin, E. F., Gould, V., Eds.; Chapman & Hall: New York; Chapter 8
-
Other scenarios have been reported where reactions with nonlinear transition states give high KIE values. The high KIE values were attributed to significant intermolecular force constants. For discussion of this concept, see: Motell, E. L.; Boone, A. W.; Fink, W. H. Tetrahedron 1978, 34, 1619-1626. Additionally, for discussion of proton-transfer reactions and KIE, see: O'Ferrall, R. A. M. In Proton-Transfer Reactions; Caldin, E. F., Gould, V., Eds.; Chapman & Hall: New York, 1975; Chapter 8.
-
(1975)
Proton-Transfer Reactions
-
-
O'Ferrall, R.A.M.1
-
67
-
-
0035810510
-
-
Andrews, L.; Wang, X.; Alikhani, M. E.; Manceron, L. J. Phys. Chem. A 2001, 105, 3052-3063.
-
(2001)
J. Phys. Chem. A
, vol.105
, pp. 3052-3063
-
-
Andrews, L.1
Wang, X.2
Alikhani, M.E.3
Manceron, L.4
-
69
-
-
3042643476
-
-
(b) While the current paper was in review, a computational model of the Pd(II)-catalyzed oxidative kinetic resolution of secondary alcohols using (-)-sparteine was reported. In this study, the authors report that the chloride ion is closely associated with the Pd(II) center (3.0 Å) at the transition state for β-hydride elimination; see: Nielsen, R. J.; Keith, J. M.; Stoltz, B. M.; Goddard, W. A., III. J. Am. Chem. Soc. 2004, 726, 7967-7974.
-
(2004)
J. Am. Chem. Soc.
, vol.726
, pp. 7967-7974
-
-
Nielsen, R.J.1
Keith, J.M.2
Stoltz, B.M.3
Goddard III, W.A.4
-
70
-
-
3543092310
-
-
note
-
Initial calculations performed on both cis- and trans-Pd(IiPr)(OAc) alkoxides (the NHC ligand was truncated) revealed the Pd complex with the alkoxide cis to the carbene ligand was found to be significantly lower in energy than the trans geometric isomer. See the Supporting Information for details.
-
-
-
-
71
-
-
0003912310
-
-
Gaussian, Inc.: Pittsburgh, PA
-
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Stratmann, R. E.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Iyengar, S.; Petersson, G. A.; Ehara, M.; Toyota, K.; Nakatsuji, H.; Adamo, C.; Jaramillo, J.; Cammi, R.; Pomelli, C.; Ochterski, J.; Ayala, P. Y.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, T.; Keith, D. J.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 01, Development Version (Revision B.01); Gaussian, Inc.: Pittsburgh, PA, 2001.
-
(2001)
Gaussian 01, Development Version (Revision B.01)
-
-
Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, J.R.6
Zakrzewski, V.G.7
Montgomery, J.A.8
Kudin, K.N.9
Burant, J.C.10
Millam, J.M.11
Stratmann, R.E.12
Tomasi, J.13
Barone, V.14
Mennucci, B.15
Cossi, M.16
Scalmani, G.17
Rega, N.18
Iyengar, S.19
Petersson, G.A.20
Ehara, M.21
Toyota, K.22
Nakatsuji, H.23
Adamo, C.24
Jaramillo, J.25
Cammi, R.26
Pomelli, C.27
Ochterski, J.28
Ayala, P.Y.29
Morokuma, K.30
Salvador, P.31
Dannenberg, J.J.32
Dapprich, S.33
Daniels, A.D.34
Strain, M.C.35
Farkas, O.36
Malick, D.K.37
Rabuck, A.D.38
Raghavachari, K.39
Foresman, J.B.40
Ortiz, J.V.41
Cui, Q.42
Baboul, A.G.43
Clifford, S.44
Cioslowski, J.45
Stefanov, B.B.46
Liu, G.47
Liashenko, A.48
Piskorz, P.49
Komaromi, I.50
Gomperts, R.51
Martin, R.L.52
Fox, T.53
Keith, D.J.54
Al-Laham, M.A.55
Peng, C.Y.56
Nanayakkara, A.57
Challacombe, M.58
Gill, P.M.W.59
Johnson, B.60
Chen, W.61
Wong, M.W.62
Andres, J.L.63
Gonzalez, C.64
Head-Gordon, M.65
Replogle, E.S.66
Pople, J.A.67
more..
-
75
-
-
0038596731
-
-
(a) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206.
-
(1989)
Chem. Phys. Lett.
, vol.157
, pp. 200-206
-
-
Miehlich, B.1
Savin, A.2
Stoll, H.3
Preuss, H.4
-
76
-
-
0345491105
-
-
(b) Lee, C.; Yang, W.; Parr, R. C. Phys. Rev. B 1988, 37, 785-789.
-
(1988)
Phys. Rev. B
, vol.37
, pp. 785-789
-
-
Lee, C.1
Yang, W.2
Parr, R.C.3
-
80
-
-
0001869943
-
-
Schaefer, H. F., III, Ed.; Plenum: New York
-
Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; pp 1-28.
-
(1976)
Modern Theoretical Chemistry
, pp. 1-28
-
-
Dunning Jr., T.H.1
Hay, P.J.2
-
81
-
-
18744407471
-
-
(a) Frenking, G.; Antes, I.; Boehme, M.; Dapprich, S.; Ehlers, A. W.; Jonas, V.; Neuhaus, A.; Otto, M.; Stegmann, R.; Veldkamp, A.; Vyboishchikov, S. F. Rev. Comput. Chem. 1996, 8, 63-143.
-
(1996)
Rev. Comput. Chem.
, vol.8
, pp. 63-143
-
-
Frenking, G.1
Antes, I.2
Boehme, M.3
Dapprich, S.4
Ehlers, A.W.5
Jonas, V.6
Neuhaus, A.7
Otto, M.8
Stegmann, R.9
Veldkamp, A.10
Vyboishchikov, S.F.11
-
82
-
-
19944380529
-
-
(b) Cundari, T. R.; Benson, M. T.; Lutz, M. L.; Sommerer, S. O. Rev. Comput. Chem. 1996, 8, 145-202.
-
(1996)
Rev. Comput. Chem.
, vol.8
, pp. 145-202
-
-
Cundari, T.R.1
Benson, M.T.2
Lutz, M.L.3
Sommerer, S.O.4
-
86
-
-
3543087648
-
-
note
-
No scaling factors were applied to frequency calculations. No solvent corrections were applied.
-
-
-
-
88
-
-
3543063124
-
-
note
-
Mulliken charges and APT charges were both calculated. The APT charges best correlated with a β-hydride elimination mechanism, Mulliken charges indicated the β-H to be more proton-like; therefore, this analysis was not used.
-
-
-
-
89
-
-
0033862728
-
-
For the reversible formation of palladium(II) hydride species under acidic conditions, see: Amatore, C.; A. Jutand, A.; Meyer, G.; Carelli, I.; Chiarotto, I. Eur. J. Inorg. Chem. 2000, 1855-1859.
-
(2000)
Eur. J. Inorg. Chem.
, pp. 1855-1859
-
-
Amatore, C.1
Jutand, A.A.2
Meyer, G.3
Carelli, I.4
Chiarotto, I.5
-
90
-
-
0034828614
-
-
2(bc) and hydrogen peroxide when exposed to acetic acid. A related Pd-bathocuproine complex was shown to be an excellent catalyst by Sheldon and co-workers for Pd-catalyzed aerobic oxidation of alcohols in aqueous conditions (see ref 17).
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 7188-7189
-
-
Stahl, S.S.1
Thorman, J.L.2
Nelson, R.C.3
Kozee, M.A.4
-
91
-
-
0000508104
-
-
John Wiley and Sons: New York
-
For a discussion on the nontriviality of Pd(0) turnover, see: Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; John Wiley and Sons: New York, 1995; p 20. For an example of Pd(0) aggregation to precipitate Pd black in the Wacker oxidation, see: Tang, H. G.; Sherrington, D. C. J. Catal. 1993, 142, 540-551.
-
(1995)
Palladium Reagents and Catalysts: Innovations in Organic Synthesis
, pp. 20
-
-
Tsuji, J.1
-
92
-
-
0000508104
-
-
For a discussion on the nontriviality of Pd(0) turnover, see: Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; John Wiley and Sons: New York, 1995; p 20. For an example of Pd(0) aggregation to precipitate Pd black in the Wacker oxidation, see: Tang, H. G.; Sherrington, D. C. J. Catal. 1993, 142, 540-551.
-
(1993)
J. Catal.
, vol.142
, pp. 540-551
-
-
Tang, H.G.1
Sherrington, D.C.2
-
93
-
-
1242352943
-
-
For recent examples, see: (a) Dewanti, A. R.; Xu, Y.; Mitra, B. Biochemistry 2004, 43, 1883-1890.
-
(2004)
Biochemistry
, vol.43
, pp. 1883-1890
-
-
Dewanti, A.R.1
Xu, Y.2
Mitra, B.3
-
95
-
-
0142031483
-
-
(c) Waas, W. F.; Rainey, M. A.; Szafranska, A. E.; Dalby, K. N. Biochemistry 2003, 42, 12273-12286.
-
(2003)
Biochemistry
, vol.42
, pp. 12273-12286
-
-
Waas, W.F.1
Rainey, M.A.2
Szafranska, A.E.3
Dalby, K.N.4
-
96
-
-
0037427416
-
-
(d) Kimura, Y.; Toyoshima, N.; Hirakawa, N.; Okamoto, K.; Ishijima, A. J. Mol. Biol. 2003, 328, 939-950.
-
(2003)
J. Mol. Biol.
, vol.328
, pp. 939-950
-
-
Kimura, Y.1
Toyoshima, N.2
Hirakawa, N.3
Okamoto, K.4
Ishijima, A.5
-
97
-
-
0034638898
-
-
(e) Fatin-Rouge, N.; Blanc, S.; Leize, E.; Van Dorsselaer, A.; Baret, P.; Pierre, J.-L.; Albrecht-Gary, A.-M. Inorg. Chem. 2000, 39, 5771-5778.
-
(2000)
Inorg. Chem.
, vol.39
, pp. 5771-5778
-
-
Fatin-Rouge, N.1
Blanc, S.2
Leize, E.3
Van Dorsselaer, A.4
Baret, P.5
Pierre, J.-L.6
Albrecht-Gary, A.-M.7
-
98
-
-
0034407333
-
-
(f) Bebelis, S.; Zeritis, A. S.; Tiropani, C.; Neophytides, S.G. Ind. Eng. Chem. Res. 2000, 39, 4920-4927.
-
(2000)
Ind. Eng. Chem. Res.
, vol.39
, pp. 4920-4927
-
-
Bebelis, S.1
Zeritis, A.S.2
Tiropani, C.3
Neophytides, S.G.4
-
99
-
-
3543111083
-
-
note
-
See the Supporting Information for details.
-
-
-
-
102
-
-
0003998388
-
-
CRC Press Inc.: Boca Raton, FL
-
a value of trifluoroacetic acid, see: Budavari, S., Ed. Merck Index, 12th ed.; Merck & Co., Inc.: Whitehouse Station, NJ, 1996.
-
(1995)
CRC Handbook of Chemistry and Physics, 75th Ed.
-
-
Lide, D.R.1
-
103
-
-
0038653828
-
-
Merck & Co., Inc.: Whitehouse Station, NJ
-
a value of trifluoroacetic acid, see: Budavari, S., Ed. Merck Index, 12th ed.; Merck & Co., Inc.: Whitehouse Station, NJ, 1996.
-
Merck Index, 12th Ed.
, pp. 1996
-
-
Budavari, S.1
-
104
-
-
3543146279
-
-
note
-
a values should lead to increases in rate. The Bronsted-type plot at 2 mol % additive carboxylic acid shows the opposite trend where carboxylate ligands with electron-donating groups show increased reaction rates. Thus, the influence of different carboxylate ligands on β-hydride elimination is probably minimal compared to the acid/base effects present.
-
-
-
|