-
3
-
-
18844392282
-
-
For mechanistic aspects, see
-
(c) For mechanistic aspects, see: Kozuch, S.; Amatore, C.; Jutand, A.; Shaik, S. Organometallics 2005, 24, 2319.
-
(2005)
Organometallics
, vol.24
, pp. 2319
-
-
Kozuch, S.1
Amatore, C.2
Jutand, A.3
Shaik, S.4
-
4
-
-
22744453412
-
-
See, for example
-
See, for example: (a) King, A. O.; Yasuda, N. Top. Organomet. Chem. 2004, 6, 205.
-
(2004)
Top. Organomet. Chem.
, vol.6
, pp. 205
-
-
King, A.O.1
Yasuda, N.2
-
5
-
-
4544270318
-
-
(b) Rouhi, A. M. Chem. Eng. News 2004, 82 (Sept. 6), 49.
-
(2004)
Chem. Eng. News
, vol.82
, Issue.SEPT. 6
, pp. 49
-
-
Rouhi, A.M.1
-
6
-
-
33745079610
-
-
especially p. 2345
-
(c) Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337; especially p. 2345.
-
(2006)
Org. Biomol. Chem.
, vol.4
, pp. 2337
-
-
Carey, J.S.1
Laffan, D.2
Thomson, C.3
Williams, M.T.4
-
7
-
-
22844452201
-
-
Review
-
Review: Wilkinson, M. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Org. Biomol. Chem. 2005, 3, 2371.
-
(2005)
Org. Biomol. Chem.
, vol.3
, pp. 2371
-
-
Wilkinson, M.J.1
Van Leeuwen, P.W.N.M.2
Reek, J.N.H.3
-
9
-
-
19044372134
-
-
(b) Shimizu, H.; Nagasaki, I.; Saito, T. Tetrahedron 2005, 61, 5405.
-
(2005)
Tetrahedron
, vol.61
, pp. 5405
-
-
Shimizu, H.1
Nagasaki, I.2
Saito, T.3
-
11
-
-
0036643424
-
-
Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69.
-
(2002)
J. Organomet. Chem.
, vol.653
, pp. 69
-
-
Hillier, A.C.1
Grasa, G.A.2
Viciu, M.S.3
Lee, H.M.4
Yang, C.5
Nolan, S.P.6
-
12
-
-
16844367937
-
-
(a) For an excellent overview and comprehensive list of references, see: Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 4685
-
-
Barder, T.E.1
Walker, S.D.2
Martinelli, J.R.3
Buchwald, S.L.4
-
13
-
-
3042654141
-
-
For additional impact of SPhos on Suzuki-Miyaura chemistry, see: (b) Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem. Int. Ed. 2004, 43, 1871.
-
(2004)
Angew. Chem. Int. Ed.
, vol.43
, pp. 1871
-
-
Walker, S.D.1
Martinelli, J.R.2
Buchwald, S.L.3
-
15
-
-
33746256441
-
-
(d) Billingsley, K. L.; Anderson, K. W.; Buchwald, S. L. Angew. Chem. Int. Ed. 2006, 45, 3484.
-
(2006)
Angew. Chem. Int. Ed.
, vol.45
, pp. 3484
-
-
Billingsley, K.L.1
Anderson, K.W.2
Buchwald, S.L.3
-
16
-
-
0037768557
-
-
1-Pd-C(ipso) interaction to the lifetime of the catalyst is being investigated, see ref. 6 and: Kočovský, P.; Vyskočil, S.; Cisařová, I.; Sejbal, J.; Tilerová, I.; Smrčina, M.; Lloyd-Jones, G. C.; Stephen, S. C.; Butts, C. P.; Murray, M.; Langer, V. J. Am. Chem. Soc. 1999, 121, 7714.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 7714
-
-
Kočovský, P.1
Vyskočil, S.2
Cisařová, I.3
Sejbal, J.4
Tilerová, I.5
Smrčina, M.6
Lloyd-Jones, G.C.7
Stephen, S.C.8
Butts, C.P.9
Murray, M.10
Langer, V.11
-
17
-
-
33645865241
-
-
(a) For an outstanding critical review on the Heck and Suzuki reactions focusing on the active species, which presents a detailed analysis of P-ligands, see: Phan, N. T. S.; Van Der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609.
-
(2006)
Adv. Synth. Catal.
, vol.348
, pp. 609
-
-
Phan, N.T.S.1
Van Der Sluys, M.2
Jones, C.W.3
-
18
-
-
33646193402
-
-
(b) For a review on hydrophilic P-based ligands, see: Shaughnessy, K. H. Eur. J. Chem. 2006, 1827.
-
(2006)
Eur. J. Chem.
, pp. 1827
-
-
Shaughnessy, K.H.1
-
20
-
-
0034714545
-
-
For a practical synthesis of biphenyl phosphine ligands using a Grignard-benzyne reaction, see: (a) Tomori, H.; Fox, J. M.; Buchwald, S. L. J. Org. Chem. 2000, 65, 5334.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 5334
-
-
Tomori, H.1
Fox, J.M.2
Buchwald, S.L.3
-
21
-
-
0035904989
-
-
For recent work, see and references cited therein
-
(b) For recent work, see: Baillie, C.; Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 9085; and references cited therein.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 9085
-
-
Baillie, C.1
Chen, W.2
Xiao, J.3
-
22
-
-
3543019095
-
-
Schenck, H. V.; Nilsson, P.; Andappan, M. S.; Larhed, M. J. Org. Chem. 2004, 69, 5212.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 5212
-
-
Schenck, H.V.1
Nilsson, P.2
Andappan, M.S.3
Larhed, M.4
-
24
-
-
33751299780
-
-
note
-
6 solution. Crystallographic data (excluding structure factors) for the structure of 4 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-609270. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK [fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk). (diagram presented) Figure 2 X-ray crystal structure of 4. For clarity, hydrogen atoms are excluded except those involved in hydrogen bonding.
-
-
-
-
25
-
-
33845378447
-
-
For similar nucleophilic aromatic substitutions driven by coordination effects, see: (a) Meyers, A. I.; Hummelsbach, R. J. J. Am. Chem. Soc. 1985, 107, 682.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 682
-
-
Meyers, A.I.1
Hummelsbach, R.J.2
-
26
-
-
1942436903
-
-
Review
-
(b) Review: Meyers, A. I.; Nelson, T. D.; Moorlag, H.; Rawson, D. J.; Merier, A. Tetrahedron 2004, 60, 4459.
-
(2004)
Tetrahedron
, vol.60
, pp. 4459
-
-
Meyers, A.I.1
Nelson, T.D.2
Moorlag, H.3
Rawson, D.J.4
Merier, A.5
-
27
-
-
33646677236
-
-
For recent work, see
-
(c) For recent work, see: Qiu, L.; Kwong, F. Y.; Wu, J.; Lam, W. H.; Chan, S.; Yu, W.-Y.; Li, Y. M.; Guo, R.; Zhou, Z.; Chan, A. S. C. J. Am. Chem. Soc. 2006, 128, 5955.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 5955
-
-
Qiu, L.1
Kwong, F.Y.2
Wu, J.3
Lam, W.H.4
Chan, S.5
Yu, W.-Y.6
Li, Y.M.7
Guo, R.8
Zhou, Z.9
Chan, A.S.C.10
-
28
-
-
0002926693
-
-
3 were also unsuccessful. See: Imamoto, T.; Kikuchi, S.; Miura, T.; Wada, Y. Org. Lett. 2001, 3, 87.
-
(2001)
Org. Lett.
, vol.3
, pp. 87
-
-
Imamoto, T.1
Kikuchi, S.2
Miura, T.3
Wada, Y.4
-
29
-
-
0028265318
-
-
and references cited therein
-
(a) Coumhe, T.; Lawrence, N. J.; Muhammad, F. Tetrahedron Lett. 1994, 35, 625; and references cited therein.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 625
-
-
Coumhe, T.1
Lawrence, N.J.2
Muhammad, F.3
-
30
-
-
33751262679
-
-
note
-
3SiH with the more economical and non-toxic polyhydromethylsiloxane (PMHS), as suggested in the above reference, was similarly effective (110 °C, 56 h) but caused problems of incomplete separation of polymeric siloxanes in column chromatography.
-
-
-
-
31
-
-
33751271368
-
-
note
-
2 ratio produced a very active catalyst, leading to 50% product formation in 15 min in DMF or MeOH at 40 °C (Table 1, entry 1).
-
-
-
-
32
-
-
3242659209
-
-
(a) Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem. Int. Ed. 2004, 43, 2206.
-
(2004)
Angew. Chem. Int. Ed.
, vol.43
, pp. 2206
-
-
Whisler, M.C.1
MacNeil, S.2
Snieckus, V.3
Beak, P.4
-
33
-
-
33748347032
-
-
Dyker, G., Ed.; Wiley-VCH: Weinheim
-
(b) Macklin, T.; Snieckus, V. In Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, 2005, 106.
-
(2005)
Handbook of C-H Transformations
, pp. 106
-
-
Macklin, T.1
Snieckus, V.2
-
34
-
-
0000439616
-
-
For previous cross-coupling of hindered benzamides which required special conditions and led to poorer yields, see: Fu, J.-m.; Sharp, M. J.; Snieckus, V. Tetrahedron Lett. 1988, 29, 5459.
-
(1988)
Tetrahedron Lett.
, vol.29
, pp. 5459
-
-
Fu, J.-M.1
Sharp, M.J.2
Snieckus, V.3
-
35
-
-
33745631204
-
-
(a) Monguchi, M.; Kume, A.; Hattori, K.; Maegawa, T.; Sajiki, H. Tetrahedron 2006, 62, 7926.
-
(2006)
Tetrahedron
, vol.62
, pp. 7926
-
-
Monguchi, M.1
Kume, A.2
Hattori, K.3
Maegawa, T.4
Sajiki, H.5
-
36
-
-
0036860845
-
-
Review
-
(b) Review: Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2002, 102, 4009.
-
(2002)
Chem. Rev.
, vol.102
, pp. 4009
-
-
Alonso, F.1
Beletskaya, I.P.2
Yus, M.3
-
37
-
-
0034034817
-
-
and refs cited therein
-
(c) Morra, M. J.; Borek, V.; Koolpe, J. J. Environ. Qual. 2000, 29, 706; and refs cited therein.
-
(2000)
J. Environ. Qual.
, vol.29
, pp. 706
-
-
Morra, M.J.1
Borek, V.2
Koolpe, J.3
-
38
-
-
0034730654
-
-
Reviews
-
Reviews: (a) Qadir, M.; Möchel, T.; Hii, K. K. Tetrahedron 2000, 56, 7975.
-
(2000)
Tetrahedron
, vol.56
, pp. 7975
-
-
Qadir, M.1
Möchel, T.2
Hii, K.K.3
-
42
-
-
33751296297
-
-
note
-
6a Nap-Phos (70%).
-
-
-
-
43
-
-
33751298781
-
-
note
-
A preliminary PM3 modeling study shows a low racemization barrier (20 kcal/mol) for Nap-Phos which precludes its use as a chiral ligand in cross coupling reactions under conditions described herein. Few chiral non-racemic atropisomeric ligand motifs are known. For discussion, see ref. 14c.
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