-
4
-
-
65749093237
-
-
Chiral bidentate NHCs have been met with more success than chiral monodentate NHCs. As notable examples, see
-
Chiral bidentate NHCs have been met with more success than chiral monodentate NHCs. As notable examples, see:
-
-
-
-
5
-
-
40149087402
-
-
Lee Y., Akiyama K., Gillingham D.G., Brown M.K., and Hoveyda A.H. J. Am. Chem. Soc. 130 (2008) 446-447
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J. Am. Chem. Soc.
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Lee, Y.1
Akiyama, K.2
Gillingham, D.G.3
Brown, M.K.4
Hoveyda, A.H.5
-
6
-
-
34250704681
-
-
Kacprzynski M.A., May T.L., Kazane S.A., and Hoveyda A.H. Angew. Chem., Int. Ed. 46 (2007) 4554-4558
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Angew. Chem., Int. Ed.
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Kacprzynski, M.A.1
May, T.L.2
Kazane, S.A.3
Hoveyda, A.H.4
-
8
-
-
34247201978
-
-
Brown M.K., May T.L., Baxter C.A., and Hoveyda A.H. Angew. Chem., Int. Ed. 46 (2007) 1097-1100
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(2007)
Angew. Chem., Int. Ed.
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, pp. 1097-1100
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Brown, M.K.1
May, T.L.2
Baxter, C.A.3
Hoveyda, A.H.4
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11
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-
4544235332
-
-
Larsen A.O., Leu W., Oberhuber C.N., Campbell J.E., and Hoveyda A.H. J. Am. Chem. Soc. 126 (2004) 11130-11131
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Larsen, A.O.1
Leu, W.2
Oberhuber, C.N.3
Campbell, J.E.4
Hoveyda, A.H.5
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12
-
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0141885397
-
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Van Veldhuizen J.J., Gillingham D.G., Garber S.B., Kataoka O., and Hoveyda A.H. J. Am. Chem. Soc. 125 (2003) 12502-12508
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J. Am. Chem. Soc.
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Van Veldhuizen, J.J.1
Gillingham, D.G.2
Garber, S.B.3
Kataoka, O.4
Hoveyda, A.H.5
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16
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0037425538
-
-
Perry M.C., Cui X., Powell M.T., Hou D.-R., Reibenspies J.H., and Burgess K. J. Am. Chem. Soc. 125 (2003) 113-123
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J. Am. Chem. Soc.
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Perry, M.C.1
Cui, X.2
Powell, M.T.3
Hou, D.-R.4
Reibenspies, J.H.5
Burgess, K.6
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17
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-
0035850506
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Powell M.T., Hou D.-R., Perry M.C., Cui X., and Burgess K. J. Am. Chem. Soc. 123 (2001) 8878-8879
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-
Powell, M.T.1
Hou, D.-R.2
Perry, M.C.3
Cui, X.4
Burgess, K.5
-
21
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-
0348050484
-
-
Ma Y., Song C., Ma C., Sun Z., Chai Q., and Andrus M.B. Angew. Chem., Int. Ed. 42 (2003) 5871-5874
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 5871-5874
-
-
Ma, Y.1
Song, C.2
Ma, C.3
Sun, Z.4
Chai, Q.5
Andrus, M.B.6
-
22
-
-
17044431761
-
-
Song C., Ma C., Ma Y., Feng W., Ma S., Chai Q., and Andrus M.B. Tetrahedron Lett. 46 (2005) 3241-3244
-
(2005)
Tetrahedron Lett.
, vol.46
, pp. 3241-3244
-
-
Song, C.1
Ma, C.2
Ma, Y.3
Feng, W.4
Ma, S.5
Chai, Q.6
Andrus, M.B.7
-
23
-
-
50849107654
-
-
Jia Y.-X., Hillgren J.M., Watson E.L., Marsden S.P., and Kündig E.P. Chem. Commun. (2008) 4040-4042
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(2008)
Chem. Commun.
, pp. 4040-4042
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-
Jia, Y.-X.1
Hillgren, J.M.2
Watson, E.L.3
Marsden, S.P.4
Kündig, E.P.5
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25
-
-
0035906503
-
-
This reaction has also been attempted with other chiral NHCs, albeit with very low enantioselectivity:
-
Lee S., and Hartwig J.F. J. Org. Chem. 66 (2001) 3402-3415 This reaction has also been attempted with other chiral NHCs, albeit with very low enantioselectivity:
-
(2001)
J. Org. Chem.
, vol.66
, pp. 3402-3415
-
-
Lee, S.1
Hartwig, J.F.2
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28
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27744557334
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Winn C.L., Guillen F., Pytkowicz J., Roland S., Mangeney P., and Alexakis A. J. Organomet. Chem. 690 (2005) 5672-5695
-
(2005)
J. Organomet. Chem.
, vol.690
, pp. 5672-5695
-
-
Winn, C.L.1
Guillen, F.2
Pytkowicz, J.3
Roland, S.4
Mangeney, P.5
Alexakis, A.6
-
29
-
-
38349171275
-
-
Sato Y., Hinata Y., Seki R., Oonishi Y., and Saito N. Org. Lett. 9 (2007) 5597-5599
-
(2007)
Org. Lett.
, vol.9
, pp. 5597-5599
-
-
Sato, Y.1
Hinata, Y.2
Seki, R.3
Oonishi, Y.4
Saito, N.5
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38
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-
24044444930
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-
Scarborough C.C., Grady M.J.W., Guzei I.A., Gandhi B.A., Bunel E.E., and Stahl S.S. Angew. Chem., Int. Ed. 44 (2005) 5269-5272
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 5269-5272
-
-
Scarborough, C.C.1
Grady, M.J.W.2
Guzei, I.A.3
Gandhi, B.A.4
Bunel, E.E.5
Stahl, S.S.6
-
40
-
-
65749105372
-
-
2 complexes appears to arise from ortho-metallation of the carboxylate complex. For a more detailed discussion, see: Rogers, M. M. Ph.D. Thesis, University of Wisconsin-Madison, Madison, WI, 2007.
-
2 complexes appears to arise from ortho-metallation of the carboxylate complex. For a more detailed discussion, see: Rogers, M. M. Ph.D. Thesis, University of Wisconsin-Madison, Madison, WI, 2007.
-
-
-
-
41
-
-
65749083845
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-
Attempts to resolve amidinium salts with methyl groups in the 3 and 3′ positions of the biphenyl moiety were unsuccessful. For further details, see: Scarborough, C.C. Ph.D. Thesis, University of Wisconsin-Madison, Madison, WI, 2008.
-
Attempts to resolve amidinium salts with methyl groups in the 3 and 3′ positions of the biphenyl moiety were unsuccessful. For further details, see: Scarborough, C.C. Ph.D. Thesis, University of Wisconsin-Madison, Madison, WI, 2008.
-
-
-
-
42
-
-
36749064861
-
-
7NHCs, Herrmann and co-workers reported that amidinium salts derived from BINAM could be accessed with secondary alkyl and aryl nitrogen substituents when phosgene was added to the mono-formylated diamine: In our hands, these amidinium salts were highly unstable to water and difficult to work with
-
7NHCs, Herrmann and co-workers reported that amidinium salts derived from BINAM could be accessed with secondary alkyl and aryl nitrogen substituents when phosgene was added to the mono-formylated diamine:. Herrmann W.A., Baskakov D., and Ruhland K. J. Heterocycl. Chem. 44 (2007) 237-239 In our hands, these amidinium salts were highly unstable to water and difficult to work with
-
(2007)
J. Heterocycl. Chem.
, vol.44
, pp. 237-239
-
-
Herrmann, W.A.1
Baskakov, D.2
Ruhland, K.3
-
44
-
-
21244438753
-
-
This reaction was inspired by an early report by Tremont and co-workers who reported a Pd-catalyzed ortho methylation of acetanilides using MeI and AgOAc:
-
Daugulis O., and Zaitsev V.G. Angew. Chem., Int. Ed. 44 (2005) 4046-4048 This reaction was inspired by an early report by Tremont and co-workers who reported a Pd-catalyzed ortho methylation of acetanilides using MeI and AgOAc:
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 4046-4048
-
-
Daugulis, O.1
Zaitsev, V.G.2
-
46
-
-
64149105444
-
-
Scarborough C.C., McDonald R.I., Hartmann C., Sazama G.T., Bergant A., and Stahl S.S. J. Org. Chem. 74 (2009) 2613-2615
-
(2009)
J. Org. Chem.
, vol.74
, pp. 2613-2615
-
-
Scarborough, C.C.1
McDonald, R.I.2
Hartmann, C.3
Sazama, G.T.4
Bergant, A.5
Stahl, S.S.6
-
47
-
-
0037123608
-
-
For the synthesis and resolution of this chiral diamine, see:
-
For the synthesis and resolution of this chiral diamine, see:. Gillespie K.M., Sanders C.J., O'Shaughnessy P., Westmoreland I., Thickitt C.P., and Scott P. J. Org. Chem. 67 (2002) 3450-3458
-
(2002)
J. Org. Chem.
, vol.67
, pp. 3450-3458
-
-
Gillespie, K.M.1
Sanders, C.J.2
O'Shaughnessy, P.3
Westmoreland, I.4
Thickitt, C.P.5
Scott, P.6
-
48
-
-
65749111629
-
-
note
-
Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. 718220 (9), 718221 ((S)-14) and 718222 (19) CCDC. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
-
-
-
-
50
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0034742920
-
-
Alder R.W., Blake M.E., Bufali S., Butts C.P., Orpen A.G., Schütz J., and Williams S.J. J. Chem. Soc., Perkin Trans. 1 (2001) 1586-1593
-
(2001)
J. Chem. Soc., Perkin Trans. 1
, pp. 1586-1593
-
-
Alder, R.W.1
Blake, M.E.2
Bufali, S.3
Butts, C.P.4
Orpen, A.G.5
Schütz, J.6
Williams, S.J.7
-
51
-
-
33344464334
-
-
The use of microwave irradiation to improve reaction times and yields in the synthesis of 5-membered amidinium salts has been demonstrated:
-
The use of microwave irradiation to improve reaction times and yields in the synthesis of 5-membered amidinium salts has been demonstrated:. Aidouni A., Demonceau A., and Delaude L. Synlett (2006) 493-495
-
(2006)
Synlett
, pp. 493-495
-
-
Aidouni, A.1
Demonceau, A.2
Delaude, L.3
-
52
-
-
44349094826
-
-
This strategy has also been applied by: In the present case, use of microwave irradiation is critical in obtaining reasonable yields of these 7-membered amidinium salts
-
This strategy has also been applied by:. Luan X., Mariz R., Gatti M., Costabile C., Poater A., Cavallo L., Linden A., and Dorta R. J. Am. Chem. Soc. 130 (2008) 6848-6858 In the present case, use of microwave irradiation is critical in obtaining reasonable yields of these 7-membered amidinium salts
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 6848-6858
-
-
Luan, X.1
Mariz, R.2
Gatti, M.3
Costabile, C.4
Poater, A.5
Cavallo, L.6
Linden, A.7
Dorta, R.8
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53
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65749112749
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Ph.D. Thesis, University of Wisconsin-Madison, Madison, WI
-
Scarborough, C.C. Ph.D. Thesis, University of Wisconsin-Madison, Madison, WI, 2008.
-
(2008)
-
-
Scarborough, C.C.1
-
54
-
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65749083083
-
-
note
-
The dimeric catalyst (S,S)-29 was used in conjunction with a silver additive in place of the monomeric catalyst (S)-30 because (S)-30 was prone to decomposition over prolonged storage periods. Control experiments in the cyclization of 2 revealed that the same results are obtained when (S,S)-29 with 4 equiv of AgTFA were employed in the catalytic mixture as when (S)-30 was employed.
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-
-
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55
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33644933443
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Yip K.-T., Yang M., Law K.-L., Zhu N.-Y., and Yang D. J. Am. Chem. Soc. 128 (2006) 3130-3131
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J. Am. Chem. Soc.
, vol.128
, pp. 3130-3131
-
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Yip, K.-T.1
Yang, M.2
Law, K.-L.3
Zhu, N.-Y.4
Yang, D.5
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57
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5244370033
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Pangborn A.B., Giardello M.A., Grubbs R.H., Rosen R.K., and Timmers F.J. Organometallics 15 (1996) 1518-1520
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(1996)
Organometallics
, vol.15
, pp. 1518-1520
-
-
Pangborn, A.B.1
Giardello, M.A.2
Grubbs, R.H.3
Rosen, R.K.4
Timmers, F.J.5
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