-
1
-
-
34248637761
-
-
For recent reviews on gold-catalyzed reactions, see: a) A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064-8105:
-
(2006)
Angew. Chem.
, vol.118
, pp. 8064-8105
-
-
Hashmi, A.S.K.1
Hutchings, G.J.2
-
2
-
-
33845546747
-
-
Angew. Chem. Int. Ed. 2006, 45, 7896-7936;
-
(2006)
Angew. Chem. Int. Ed.
, vol.45
, pp. 7896-7936
-
-
-
3
-
-
51049121927
-
-
b) Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239-3265;
-
(2008)
Chem. Rev.
, vol.108
, pp. 3239-3265
-
-
Li, Z.1
Brouwer, C.2
He, C.3
-
4
-
-
51049105959
-
-
c) D. J. Gorin, B.D. Sherry, F.D. Toste, Chem. Rev. 2008, 108, 3351-3378;
-
(2008)
Chem. Rev.
, vol.108
, pp. 3351-3378
-
-
Gorin, D.J.1
Sherry, B.D.2
Toste, F.D.3
-
5
-
-
46749159211
-
-
d) H.C. Shen, Tetrahedron 2008, 64, 7847-7870;
-
(2008)
Tetrahedron
, vol.64
, pp. 7847-7870
-
-
Shen, H.C.1
-
8
-
-
34250840234
-
-
b) I. Nakamura, T. Sato, Y. Yamamoto, Angew. Chem. 2006, 118, 4585-4587;
-
(2006)
Angew. Chem.
, vol.118
, pp. 4585-4587
-
-
Nakamura, I.1
Sato, T.2
Yamamoto, Y.3
-
9
-
-
33746309818
-
-
Angew. Chem. Int. Ed. 2006, 45, 4473-4475;
-
(2006)
Angew. Chem. Int. Ed.
, vol.45
, pp. 4473-4475
-
-
-
10
-
-
59949103940
-
-
c) I. Nakamura, T. Sato, M. Terada, Y. Yamamoto, Org. Lett. 2008, 13, 2649-2651;
-
(2008)
Org. Lett.
, vol.13
, pp. 2649-2651
-
-
Nakamura, I.1
Sato, T.2
Terada, M.3
Yamamoto, Y.4
-
11
-
-
70249142536
-
-
d) M. Uemura, I. D. G. Watson, M. Katsukawa, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 3464-3465;
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 3464-3465
-
-
Uemura, M.1
Watson, I.D.G.2
Katsukawa, M.3
Toste, F.D.4
-
12
-
-
73249139585
-
-
e) A. N. Se, J. Jeong, B. Baskar, J. Lee, Y. H. Rhee, Chem. Eur. J. 2009, 15, 11837-11841.
-
(2009)
Chem. Eur. J
, vol.15
, pp. 11837-11841
-
-
Se, A.N.1
Jeong, J.2
Baskar, B.3
Lee, J.4
Rhee, Y.H.5
-
13
-
-
4344653148
-
-
a) C. Nieto-Oberhuber, M. P. Muñiz, E. Bunuel, C. Nevado, D. J. Cardenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460;
-
(2004)
Angew. Chem.
, vol.116
, pp. 2456-2460
-
-
Nieto-Oberhuber, C.1
Muñiz, M.P.2
Bunuel, E.3
Nevado, C.4
Cardenas, D.J.5
Echavarren, A.M.6
-
14
-
-
3242741475
-
-
Angew. Chem. Int. Ed. 2004, 43, 2402-2406;
-
(2004)
Angew. Chem. Int. Ed.
, vol.43
, pp. 2402-2406
-
-
-
15
-
-
29844455305
-
-
b) M. J. Johansson, D. J. Gorin, S. T. Staben, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 18002-18003;
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 18002-18003
-
-
Johansson, M.J.1
Gorin, D.J.2
Staben, S.T.3
Toste, F.D.4
-
16
-
-
33845772273
-
-
c) S. López, E. Herrero-Gomez, P. Perez-Galan, C. Nieto-Oberhuber, A. M. Echavarren, Angew. Chem. 2006, 118, 6175-6178;
-
(2006)
Angew. Chem.
, vol.118
, pp. 6175-6178
-
-
López, S.1
Herrero-Gomez, E.2
Perez-Galan, P.3
Nieto-Oberhuber, C.4
Echavarren, A.M.5
-
17
-
-
33748792796
-
-
Angew. Chem. Int. Ed. 2006, 45, 6029-6032;
-
(2006)
Angew. Chem. Int. Ed.
, vol.45
, pp. 6029-6032
-
-
-
19
-
-
34248597739
-
-
e) C. A. Witham, P. Mauleón, N. D. Shapiro, D. B. Sherry, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 5838-5839;
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 5838-5839
-
-
Witham, C.A.1
Mauleón, P.2
Shapiro, N.D.3
Sherry, D.B.4
Toste, F.D.5
-
20
-
-
35048842179
-
-
f) C. H. M. Amijs, V. Opez-Carrillo, A. M. Echavarren, Org. Lett. 2007, 9, 4021-4024;
-
(2007)
Org. Lett.
, vol.9
, pp. 4021-4024
-
-
Amijs, C.H.M.1
Opez-Carrillo, V.2
Echavarren, A.M.3
-
21
-
-
54749142526
-
-
g) M. Schelwies A. L. Dempwolff, F. Rominger, G. Helmchen, Angew. Chem. 2007, 119, 5694-5697;
-
(2007)
Angew. Chem.
, vol.119
, pp. 5694-5697
-
-
Schelwies, M.1
Dempwolff, A.L.2
Rominger, F.3
Helmchen, G.4
-
22
-
-
34547183880
-
-
Angew. Chem. Int. Ed. 2007, 46, 5598-5601;
-
(2007)
Angew. Chem. Int. Ed.
, vol.46
, pp. 5598-5601
-
-
-
24
-
-
53049091331
-
-
i) C. H. M. Amijs, V. Lopez-Carrillo, M. Raducan, P. Perez-Galan, C. Ferrer, A. M. Echavarren, J. Org. Chem. 2008, 73, 7721-7730;
-
(2008)
J. Org. Chem.
, vol.73
, pp. 7721-7730
-
-
Amijs, C.H.M.1
Lopez-Carrillo, V.2
Raducan, M.3
Perez-Galan, P.4
Ferrer, C.5
Echavarren, A.M.6
-
25
-
-
75249096472
-
-
j) A. S. K. Hashmi, C. Lothschütz, R. Döpp, M. Rudolph, T. D. Ramamurthi, F. Rominger, Angew. Chem. 2009, 121, 8392-8395;
-
(2009)
Angew. Chem.
, vol.121
, pp. 8392-8395
-
-
Hashmi, A.S.K.1
Lothschütz, C.2
Döpp, R.3
Rudolph, M.4
Ramamurthi, T.D.5
Rominger, F.6
-
26
-
-
70350031641
-
-
Angew. Chem. Int. Ed. 2009, 48, 8243-8246;
-
(2009)
Angew. Chem. Int. Ed.
, vol.48
, pp. 8243-8246
-
-
-
27
-
-
72449169570
-
-
k) Y. Shi, K. E. Roth, S. D. Ramgren, S. A. Blum, J. Am. Chem. Soc. 2009, 131, 18022-18023.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 18022-18023
-
-
Shi, Y.1
Roth, K.E.2
Ramgren, S.D.3
Blum, S.A.4
-
28
-
-
37849017473
-
-
a) A. Kar, N. Mangu, H. M. Kaiser, M. Beller, M. K. Tse, Chem. Commun. 2008, 386-388;
-
(2008)
Chem. Commun.
, pp. 386-388
-
-
Kar, A.1
Mangu, N.2
Kaiser, H.M.3
Beller, M.4
Tse, M.K.5
-
29
-
-
58649097938
-
-
b) A. S. K. Hashmi, T. D. Ramamurthi, F. Rominger, J. Organomet. Chem. 2009, 694, 592-597;
-
(2009)
J. Organomet. Chem.
, vol.694
, pp. 592-597
-
-
Hashmi, A.S.K.1
Ramamurthi, T.D.2
Rominger, F.3
-
30
-
-
70350008287
-
-
c) G. Zhang, Y. Peng, L. Cui, L. Zhang, Angew. Chem. 2009, 121, 3158-3161;
-
(2009)
Angew. Chem.
, vol.121
, pp. 3158-3161
-
-
Zhang, G.1
Peng, Y.2
Cui, L.3
Zhang, L.4
-
31
-
-
70349782130
-
-
Angew. Chem. Int. Ed. 2009, 48, 3112-3115;
-
(2009)
Angew. Chem. Int. Ed.
, vol.48
, pp. 3112-3115
-
-
-
33
-
-
76149131690
-
-
e) After submission of the original version of this manuscript, the following communication was reported: G. Zhang, L. Cui, Y. Wang, L. Zhang, J. Am. Chem. Soc. 2010, 132, 1474-1475;
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 1474-1475
-
-
Zhang, G.1
Cui, L.2
Wang, Y.3
Zhang, L.4
-
34
-
-
53149142729
-
-
f) For a review of oxidation-reduction reactions of gold complexes, see: V. P. Dyadchenko, Russ Chem. Rev. 1982, 57, 265.
-
(1982)
Russ Chem. Rev.
, vol.57
, pp. 265
-
-
Dyadchenko, V.P.1
-
35
-
-
33847664670
-
-
a) R. L. Lalonde, B. D. Sherry, E. J. Kang, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 2452-2453;
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 2452-2453
-
-
Lalonde, R.L.1
Sherry, B.D.2
Kang, E.J.3
Toste, F.D.4
-
36
-
-
34547567515
-
-
b) G. L. Hamilton, E. J. Kang, M. Mba, F.D. Toste, Science 2007, 317, 496-499;
-
(2007)
Science
, vol.317
, pp. 496-499
-
-
Hamilton, G.L.1
Kang, E.J.2
Mba, M.3
Toste, F.D.4
-
37
-
-
77953919384
-
-
c) R. L. LaLonde, Z. J. Wang, A. D. Lackner, F. D. Toste, Angew. Chem. 2010, 122, 608-611;
-
(2010)
Angew. Chem.
, vol.122
, pp. 608-611
-
-
LaLonde, R.L.1
Wang, Z.J.2
Lackner, A.D.3
Toste, F.D.4
-
40
-
-
27544494421
-
-
For related transition-metal-catalyzed aminoarylation reactions, see: a) J. E. Ney, J. P. Wolfe, Angew. Chem. 2004, 116, 3689-3692;
-
(2004)
Angew. Chem.
, vol.116
, pp. 3689-3692
-
-
Ney, J.E.1
Wolfe, J.P.2
-
41
-
-
4544265647
-
-
Angew. Chem. Int. Ed. 2004, 43, 3605-3608;
-
(2004)
Angew. Chem. Int. Ed.
, vol.43
, pp. 3605-3608
-
-
-
43
-
-
33847074190
-
-
c) M. B. Bertrand, M. L. Leathen, J. P. Wolfe, Org. Lett. 2007, 9, 457-460;
-
(2007)
Org. Lett.
, vol.9
, pp. 457-460
-
-
Bertrand, M.B.1
Leathen, M.L.2
Wolfe, J.P.3
-
44
-
-
56449098619
-
-
d)M. B. Bertrand, J. D. Neukum, J. P. Wolfe, J. Org. Chem. 2008, 73, 8851-8860;
-
(2008)
J. Org. Chem.
, vol.73
, pp. 8851-8860
-
-
Bertrand, M.B.1
Neukum, J.D.2
Wolfe, J.P.3
-
45
-
-
67650507268
-
-
e) C.F. Rosewall, P.A. Sibbald, D.V. Liskin, F. E. Michael, J. Am. Chem. Soc. 2009, 131, 9488-9489;
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 9488-9489
-
-
Rosewall, C.F.1
Sibbald, P.A.2
Liskin, D.V.3
Michael, F.E.4
-
46
-
-
70350662846
-
-
f) P. A. Sibbald, C. F. Rosewall, R. D. Schwartz, F. E. Michael, J. Am. Chem. Soc. 2009, 131, 15945-15951.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 15945-15951
-
-
Sibbald, P.A.1
Rosewall, C.F.2
Schwartz, R.D.3
Michael, F.E.4
-
49
-
-
67949109328
-
-
For recent examples of oxidative transformations catalyzed by bimetallic complexes, see: a) D. C. Powers, T. Ritter, Nat. Chem. 2009, 1, 302-309;
-
(2009)
Nat. Chem.
, vol.1
, pp. 302-309
-
-
Powers, D.C.1
Ritter, T.2
-
51
-
-
72249115788
-
-
c) D. C. Powers, M. A. L. Geibel, J. E. M. N. Klein, T. Ritter, J. Am. Chem. Soc. 2009, 131, 17050-17051.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 17050-17051
-
-
Powers, D.C.1
Geibel, M.A.L.2
Klein, J.E.M.N.3
Ritter, T.4
-
52
-
-
77955025059
-
-
2]-catalyzed reaction produced 2 in only 37% yield. For full details of catalysts examined, see the Supporting Information
-
2]-catalyzed reaction produced 2 in only 37% yield. For full details of catalysts examined, see the Supporting Information.
-
-
-
-
53
-
-
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-
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31P NMR spectrum
-
31P NMR spectrum.
-
-
-
-
54
-
-
81355150856
-
-
DOI: 10.1039/c0sc00255k
-
R. L. LaLonde, W. E. Brenzovich Jr., D. Benitez, E. Tkatchouk, K. Kelley, W. A. Goddard III, F. D. Toste, Chem. Sci. 2010, DOI: 10.1039/c0sc00255k.
-
(2010)
Chem. Sci.
-
-
LaLonde, R.L.1
Brenzovich Jr., W.E.2
Benitez, D.3
Tkatchouk, E.4
Kelley, K.5
Goddard III, W.A.6
Toste, F.D.7
-
55
-
-
54849170400
-
-
D. V. Partyka, M. Zeller, A. D. Hunter, T. G. Gray, Angew. Chem, 2006, 118, 8368-8371;
-
(2006)
Angew. Chem
, vol.118
, pp. 8368-8371
-
-
Partyka, D.V.1
Zeller, M.2
Hunter, A.D.3
Gray, T.G.4
-
56
-
-
84962374620
-
-
Angew. Chem. Int. Ed. 2006, 45, 8188-8191.
-
(2006)
Angew. Chem. Int. Ed.
, vol.45
, pp. 8188-8191
-
-
-
57
-
-
0000831827
-
-
a) A. Tamaki, S. A. Magennis, J. K. Kochi, J. Am. Chem. Soc. 1974, 96, 6140-6148;
-
(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 6140-6148
-
-
Tamaki, A.1
Magennis, S.A.2
Kochi, J.K.3
-
58
-
-
33847798583
-
-
b) S. Komiya, TA. Albright, R. Hoffmann, J. K. Kochi, J. Am. Chem. Soc. 1976, 98, 7255-7265;
-
(1976)
J. Am. Chem. Soc.
, vol.98
, pp. 7255-7265
-
-
Komiya, S.1
Albright, T.A.2
Hoffmann, R.3
Kochi, J.K.4
-
62
-
-
35348955794
-
-
f) C. González-Arellano, A. Abad, A. Corma, H. García, M. Iglesias, F. Sánchez, Angew. Chem. 2007, 119, 1558-1560;
-
(2007)
Angew. Chem.
, vol.119
, pp. 1558-1560
-
-
González-Arellano, C.1
Abad, A.2
Corma, A.3
García, H.4
Iglesias, M.5
Sánchez, F.6
-
63
-
-
34250755002
-
-
Angew. Chem, Int. Ed. 2007, 46, 1536-1538.
-
(2007)
Angew. Chem, Int. Ed.
, vol.46
, pp. 1536-1538
-
-
-
64
-
-
77955021859
-
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3PAuPh provides 2 from 1 in 31 % yield. See the Supporting Information for more details
-
3PAuPh provides 2 from 1 in 31 % yield. See the Supporting Information for more details.
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65
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77955036702
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note
-
Ongoing theoretical (DFT) investigations support this type of a nucleophilic reductive elimination pathway. Relaxed coordinate scans suggest a concerted reductive elimination process, in which the B-F bond is formed prior to the C-C bond, thus effectively achieving regeneration of the catalyst and product demetalation. In contrast, we could not find a pathway for transmetalation, in which the phenyl group is transferred onto the gold center, thereby leading to the formation of alkylphenylgold(III) intermediate 32.
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66
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-
-
For examples of syn-aminopalladation see: a) J. D. Neukon, N. S. Perch, J. P. Wolfe, J. Am. Chem. Soc. 2010, 132, 6276-6277;
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 6276-6277
-
-
Neukon, J.D.1
Perch, N.S.2
Wolfe, J.P.3
-
68
-
-
77955043784
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For an example of anti-aminopalladation see Ref. [7f]
-
For an example of anti-aminopalladation see Ref. [7f].
-
-
-
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69
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77955029773
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For full details and analysis, see the Supporting Information
-
For full details and analysis, see the Supporting Information.
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