-
5
-
-
34948896140
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-
Reference 2a
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(a) Reference 2a.
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-
-
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8
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34250797354
-
-
For a recent review of palladium complexes with NHC ligands, see
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For a recent review of palladium complexes with NHC ligands, see: Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Angew. Chem., Int. Ed. 2007, 46, 2768-2813.
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Angew. Chem., Int. Ed
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Kantchev, E.A.B.1
O'Brien, C.J.2
Organ, M.G.3
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9
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8344265265
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For a review, see
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For a review, see: Szabó, K. J. Chem.-Eur. J. 2004, 10, 5268-5275.
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(2004)
Chem.-Eur. J
, vol.10
, pp. 5268-5275
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Szabó, K.J.1
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12
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0037986275
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Allylpalladium complexes ligated by NHC ligands undergo protonolysis reactions with HCl where the allyl ligand presumably acts as a nucleophile: Jensen, D. R, Sigman, M. S. Org. Lett. 2003, 5, 63-65
-
Allylpalladium complexes ligated by NHC ligands undergo protonolysis reactions with HCl where the allyl ligand presumably acts as a nucleophile: Jensen, D. R.; Sigman, M. S. Org. Lett. 2003, 5, 63-65.
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-
-
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13
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34948901548
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Yamamoto, Y.; Nakamura, I. In Palladium in Organic Synthesis; Tsuji, J., Ed.; Topics in Organometallic Chemistry 14; Springer-Verlag: New York, 2005; 14, pp 211-239.
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(a) Yamamoto, Y.; Nakamura, I. In Palladium in Organic Synthesis; Tsuji, J., Ed.; Topics in Organometallic Chemistry 14; Springer-Verlag: New York, 2005; Vol. 14, pp 211-239.
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14
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0242497940
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and references therein
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(b) Fernandes, R. A.; Stimac, A.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 14133-14139, and references therein.
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J. Am. Chem. Soc
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Fernandes, R.A.1
Stimac, A.2
Yamamoto, Y.3
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(a) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641-6647.
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J. Am. Chem. Soc
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Nakamura, H.1
Iwama, H.2
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3042774302
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(a) Solin, N.; Kjellgren, J.; Szabó, K. J. J. Am. Chem. Soc. 2004, 126, 7026-7033.
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J. Am. Chem. Soc
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Solin, N.1
Kjellgren, J.2
Szabó, K.J.3
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18
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0042969402
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(b) Solin, N.; Kjellgren, J.; Szabó, K. J. Angew. Chem., Int. Ed. 2003, 42, 3656-3658.
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Angew. Chem., Int. Ed
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Solin, N.1
Kjellgren, J.2
Szabó, K.J.3
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19
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34249785407
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For DFT calculations supporting a Sakurai-type mechanism for this reaction, see
-
(c) For DFT calculations supporting a Sakurai-type mechanism for this reaction, see: Piechaczyk, O.; Cantat, T.; Mézailles, N.; Le Floch, P. J. Org. Chem. 2007, 72, 4228-4237.
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(2007)
J. Org. Chem
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Piechaczyk, O.1
Cantat, T.2
Mézailles, N.3
Le Floch, P.4
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20
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33645308290
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-
For other examples of reactions that are thought to proceed via nucleophilic allylpalladium intermediates, see: (a) Howell, G. P, Minnaard, A. J, Feringa, B. L. Org. Biomol. Chem. 2006, 4, 1278-1283
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For other examples of reactions that are thought to proceed via nucleophilic allylpalladium intermediates, see: (a) Howell, G. P.; Minnaard, A. J.; Feringa, B. L. Org. Biomol. Chem. 2006, 4, 1278-1283.
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-
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23
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34948893587
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An alternate strategy developed for palladium-catalyzed umpolung allylation of electrophiles likely involves transmetalation to Zn, B, In, or Sn. For a lead reference, see: Tamaru, Y. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I, Ed, Wiley-Interscience: New York, 2002; 2, p 1917
-
An alternate strategy developed for palladium-catalyzed umpolung allylation of electrophiles likely involves transmetalation to Zn, B, In, or Sn. For a lead reference, see: Tamaru, Y. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley-Interscience: New York, 2002; Vol. 2, p 1917.
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24
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18444411670
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See Supporting Information for details, (a) Complex 4a: Jones, M. D.; Paz, F. A. A.; Davies. J. E.; Johnson, B. F. G.; Klinowski, J. Acta Crystallogr., Sect. E: Struct. Rep. Online 2003, E59, M538-M540.
-
See Supporting Information for details, (a) Complex 4a: Jones, M. D.; Paz, F. A. A.; Davies. J. E.; Johnson, B. F. G.; Klinowski, J. Acta Crystallogr., Sect. E: Struct. Rep. Online 2003, E59, M538-M540.
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25
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85152991479
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Complex 4b: Malaisé, G.; Shailesh, R.; Osborn, J. A.; Barloy, L.; Kyritsakas, N.; Graff, R. Eur. J. Inorg. Chem. 2004, 3987-4001.
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(b) Complex 4b: Malaisé, G.; Shailesh, R.; Osborn, J. A.; Barloy, L.; Kyritsakas, N.; Graff, R. Eur. J. Inorg. Chem. 2004, 3987-4001.
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26
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31544483930
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Complex 4c: Navarro, O.; Nolan, S. P. Synthesis 2006, 2, 366-367.
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(c) Complex 4c: Navarro, O.; Nolan, S. P. Synthesis 2006, 2, 366-367.
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27
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0000004671
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Formation of silver carbenes: Wang, H. M. J.; Lin, I. J. B. Organometallics 1998, 17, 972.
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(d) Formation of silver carbenes: Wang, H. M. J.; Lin, I. J. B. Organometallics 1998, 17, 972.
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28
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0042031145
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Counterion exchange: Viciu, M. S.; Kauer, Z. F.; Stevens, E. D.; Nolan, S. P. Organometallics 2003, 22, 3175-3177.
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(e) Counterion exchange: Viciu, M. S.; Kauer, Z. F.; Stevens, E. D.; Nolan, S. P. Organometallics 2003, 22, 3175-3177.
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29
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0001474120
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Bidentate NHC ligands and complexes 4d-m: (a) Magill, A. M.; McGuinness, D. S.; Cavell, K. J.; Britovsek, G. J. P.; Gibson, V. C.; White, A. J. P.; Williams, D. J.; White, A. H.; Skelton, B. W. J. Organomet. Chem. 2001, 617-618, 546-560.
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Bidentate NHC ligands and complexes 4d-m: (a) Magill, A. M.; McGuinness, D. S.; Cavell, K. J.; Britovsek, G. J. P.; Gibson, V. C.; White, A. J. P.; Williams, D. J.; White, A. H.; Skelton, B. W. J. Organomet. Chem. 2001, 617-618, 546-560.
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31
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33846646522
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(c) Danopoulos, A. A.; Tsoureas, N.; Macgregor, S. A.; Smith, C. Organometallics 2007, 23, 253-263.
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(2007)
Organometallics
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, pp. 253-263
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Danopoulos, A.A.1
Tsoureas, N.2
Macgregor, S.A.3
Smith, C.4
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32
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23844524140
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(d) Field, L. D.; Messerle, B. A.; Vuong, K. Q.; Turner, P. Organometallics 2005, 24, 4241-4250.
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(2005)
Organometallics
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, pp. 4241-4250
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Field, L.D.1
Messerle, B.A.2
Vuong, K.Q.3
Turner, P.4
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33
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0001273662
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(e) Yang, C.; Lee, H. M.; Nolan, S. P. Org. Lett. 2001, 3, 1511-1514.
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(2001)
Org. Lett
, vol.3
, pp. 1511-1514
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Yang, C.1
Lee, H.M.2
Nolan, S.P.3
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34
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0345015851
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(f) Tsoureas, N.; Danopoulos, A. A.; Tulloch, A. A. D.; Light, M. E. Organometallics 2003, 22, 4750-4758.
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(2003)
Organometallics
, vol.22
, pp. 4750-4758
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Tsoureas, N.1
Danopoulos, A.A.2
Tulloch, A.A.D.3
Light, M.E.4
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36
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0003466377
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Jackman, L. M, Cotton, F. A, Eds, Academic Press: New York
-
(b) Vrieze, K. In Dynamic Nuclear Magnetic Resonance Spectroscopy; Jackman, L. M., Cotton, F. A., Eds.; Academic Press: New York, 1975.
-
(1975)
Dynamic Nuclear Magnetic Resonance Spectroscopy
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Vrieze, K.1
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38
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0037458327
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For the crystal structure of related complexes, see: a
-
For the crystal structure of related complexes, see: (a) Tulloch, A. A. D.; Winston, S.; Danopoulos, A. A.; Eastham, G.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 2003, 699-708.
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(2003)
J. Chem. Soc., Dalton Trans
, pp. 699-708
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Tulloch, A.A.D.1
Winston, S.2
Danopoulos, A.A.3
Eastham, G.4
Hursthouse, M.B.5
-
39
-
-
34948815751
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Reference 14c
-
(b) Reference 14c.
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-
-
-
41
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34948908294
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Phosphonium salts, formed by nucleophilic attack of phosphine ligand on the allylpalladium, are formed as the major decomposition products when nucleophilic phosphines are employed
-
Phosphonium salts, formed by nucleophilic attack of phosphine ligand on the allylpalladium, are formed as the major decomposition products when nucleophilic phosphines are employed.
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-
-
-
42
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34948869980
-
-
Products that would arise from β-hydride elimination of the palladium alkoxide, such as 1-phenyl-3-butenone or 1 -pheny 1-2-butenone, were not observed
-
Products that would arise from β-hydride elimination of the palladium alkoxide, such as 1-phenyl-3-butenone or 1 -pheny 1-2-butenone, were not observed.
-
-
-
-
43
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34948834854
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-
See reference 3c
-
See reference 3c.
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-
-
-
44
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0000719130
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-
Kurosawa, H.; Urabe, A.; Kasai, N. Organometallics 1986, 5, 2002-2006.
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(1986)
Organometallics
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, pp. 2002-2006
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Kurosawa, H.1
Urabe, A.2
Kasai, N.3
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45
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0035833309
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Braunstein, P.; Naud, F.; Dedieu, A.; Rohmer, M.-M.; DeCian, A.; Rettig, S. J. Organometallics 2001, 20, 2966-2981.
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(2001)
Organometallics
, vol.20
, pp. 2966-2981
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Braunstein, P.1
Naud, F.2
Dedieu, A.3
Rohmer, M.-M.4
DeCian, A.5
Rettig, S.J.6
-
46
-
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0037016413
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-
For a review of halide effects in transition metal catalysis, see
-
For a review of halide effects in transition metal catalysis, see: Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 26-47.
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(2002)
Angew. Chem., Int. Ed
, vol.41
, pp. 26-47
-
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Fagnou, K.1
Lautens, M.2
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47
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2942700115
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The cause of this effect is under investigation and is presumably due to the differing ability of the solvents to coordinate to palladium complex Ih, a Ketz, B. E, Cole, A. P, Waymouth, R. M. Organometallics 2004, 23, 2835-2837
-
The cause of this effect is under investigation and is presumably due to the differing ability of the solvents to coordinate to palladium complex Ih. (a) Ketz, B. E.; Cole, A. P.; Waymouth, R. M. Organometallics 2004, 23, 2835-2837.
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49
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3042774302
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This trend may be due to the differing rates of transmetalation of the palladium alkoxides with allyltributylstannane. In related allylation reactions a decrease in rate with increasing electron-donating ability of pincer ligands has been attributed to a decrease in the rate of transmetalation: Solin, N, Kjellgren, J, Szabó, K. J. J. Am. Chem. Soc. 2004, 126, 7026-7033
-
This trend may be due to the differing rates of transmetalation of the palladium alkoxides with allyltributylstannane. In related allylation reactions a decrease in rate with increasing electron-donating ability of pincer ligands has been attributed to a decrease in the rate of transmetalation: Solin, N.; Kjellgren, J.; Szabó, K. J. J. Am. Chem. Soc. 2004, 126, 7026-7033.
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-
-
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50
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34948812656
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At this time we are unable to rule out an alternate Sakurai-type mechanism, where the palladium complex functions as a Lewis acid catalyst to activate the aldehyde toward addition of allylstannane, a For a discussion, see ref 10c
-
At this time we are unable to rule out an alternate Sakurai-type mechanism, where the palladium complex functions as a Lewis acid catalyst to activate the aldehyde toward addition of allylstannane. (a) For a discussion, see ref 10c.
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