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1
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77950845245
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For a general review of cross-coupling chemistry, see:, 2nd ed, (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, New York
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For a general review of cross-coupling chemistry, see: Met al.-Catalyzed Cross Coupling Reactions, 2nd ed. (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, New York, 2004.
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Met Al.-Catalyzed Cross Coupling Reactions
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Selected recent reviews on the use of tertiary phosphanes in crosscoupling: a)
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Selected recent reviews on the use of tertiary phosphanes in crosscoupling: a) R. Martin, S. L. Buchwald, Acc. Chem. Res. 2008, 41, 1461-1473;
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Selected recent reviews on the use of NHCs in cross-coupling: a)
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Selected recent reviews on the use of NHCs in cross-coupling: a) N. Marion, S. P. Nolan, Acc. Chem. Res. 2008, 41, 1440-1449;
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Acc. Chem. Res.
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Marion, N.1
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E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Angew. Chem. 2007, 119, 2824-2870;
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Kantchev, E.A.B.1
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11
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84908659806
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For a review on late-transition-met al. catalysis using NHC-based met al. complexes, see
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For a review on late-transition-met al. catalysis using NHC-based met al. complexes, see: S. Díez-González, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612-3676.
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Chem. Rev.
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Díez-González, S.1
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Nolan, S.P.3
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12
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22744440267
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0 species as active catalysts, see
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0 species as active catalysts, see: U. Christmann, R. Vilar, Angew. Chem. 2005, 117, 370-378;
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Christmann, U.1
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0038495996
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a) M. S. Viciu, R. F. Germaneau, O. Navarro-Fernandez, E. D. Stevens, S. P. Nolan, Organomet al.lics 2002, 21, 5470-5472;
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Organomet al.lics
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Viciu, M.S.1
Germaneau, R.F.2
Navarro-Fernandez, O.3
Stevens, E.D.4
Nolan, S.P.5
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15
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0013308257
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M. S. Viciu, R. F. Germaneau, S. P. Nolan, Org. Lett. 2002, 4, 4053-4056;
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Org. Lett.
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Viciu, M.S.1
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Nolan, S.P.3
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16
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0345305249
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N. Marion, O. Navarro, R. A. Kelly, III., S. P. Nolan, Synthesis 2003, 2590-2592;
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(2003)
Synthesis
, pp. 2590-2592
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Marion, N.1
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Nolan, S.P.4
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17
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1842740885
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M. S. Viciu, O. Navarro, R. F. Germaneau, R. A. Kelly, III., W. Sommer, N. Marion, E. D. Stevens, L. Cavallo, S. P. Nolan, Organomet al.lics 2004, 23, 1629-1635;
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(2004)
Organomet al.lics
, vol.23
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Viciu, M.S.1
Navarro, O.2
Germaneau, R.F.3
Kelly, R.A.I.4
Sommer, W.5
Marion, N.6
Stevens, E.D.7
Cavallo, L.8
Nolan, S.P.9
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19
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33751515622
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C. Fliedel, A. Maisse-François, S. Bellemin-Laponnaz, Inorg. Chim. Acta 2007, 360, 143-148.
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Inorg. Chim. Acta
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Fliedel, C.1
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Bellemin-Laponnaz, S.3
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20
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33645451955
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a) N. Marion, O. Navarro, J. Mei, N. M. Scott, E. D. Stevens, S. P. Nolan, J. Am. Chem. Soc. 2006, 128, 4101-4111;
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J. Am. Chem. Soc.
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Marion, N.1
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Scott, N.M.4
Stevens, E.D.5
Nolan, S.P.6
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21
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33745728743
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For related work, see
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O. Navarro, N. Marion, J. Mei, S. P. Nolan, Chem. Eur. J. 2006, 12, 5142-5148. For related work, see:
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(2006)
Chem. Eur. J.
, vol.12
, pp. 5142-5148
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Navarro, O.1
Marion, N.2
Mei, J.3
Nolan, S.P.4
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22
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48949100374
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B. H. Lipshutz, T. B. Petersen, A. R. Abela, Org. Lett. 2008, 10, 1333-1336.
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(2008)
Org. Lett.
, vol.10
, pp. 1333-1336
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Lipshutz, B.H.1
Petersen, T.B.2
Abela, A.R.3
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23
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30744453567
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a) O. Navarro, N. Marion, Y. Oonishi, R. A. Kelly, III, S. P. Nolan, J. Org. Chem. 2006, 71, 685-692;
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(2006)
J. Org. Chem.
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Navarro, O.1
Marion, N.2
Oonishi, Y.3
Kelly, R.A.I.4
Nolan, S.P.5
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24
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0345802559
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O. Navarro, R. A. Kelly, III, S. P. Nolan, J. Am. Chem. Soc. 2003, 125, 16194-16195.
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J. Am. Chem. Soc.
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Navarro, O.1
Kelly, R.A.I.2
Nolan, S.P.3
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25
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24344490401
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a) O. Navarro, N. Marion, E. D. Stevens, N. M. Scott, J. González, D. Amoroso, A. Bell, S. P. Nolan, Tetrahedron 2005, 61, 9716-9722;
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(2005)
Tetrahedron
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Navarro, O.1
Marion, N.2
Stevens, E.D.3
Scott, N.M.4
González, J.5
Amoroso, D.6
Bell, A.7
Nolan, S.P.8
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26
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35948989669
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N. Marion, P. de Frémont, I. M. Puijk, E. C. Ecarnot, D. Amoroso, A. Bell, S. P. Nolan, Adv. Synth. Catal. 2007, 349, 2380-2384.
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Adv. Synth. Catal
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Marion, N.1
De Frémont, P.2
Puijk, I.M.3
Ecarnot, E.C.4
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Bell, A.6
Nolan, S.P.7
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27
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N. Marion, E. C. Ecarnot, O. Navarro, D. Amoroso, A. Bell, S. P. Nolan, J. Org. Chem. 2006, 71, 3816-3821.
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J. Org. Chem.
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Marion, N.1
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Nolan, S.P.6
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28
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70349777583
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Navarro and co-workers recently reported the synthesis of [(SIPr) Pd (acac) Cl], which proved to be more active in cross-coupling than 4; see
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Navarro and co-workers recently reported the synthesis of [(SIPr) Pd (acac) Cl], which proved to be more active in cross-coupling than 4; see: O. H. Winkelmann, A. Riekstins, S. P. Nolan, O. Navarro, Organomet al.lics 2009, 28, 5809-5813.
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(2009)
Organomet al.lics
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Winkelmann, O.H.1
Riekstins, A.2
Nolan, S.P.3
Navarro, O.4
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29
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10144222904
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0 point to a similar effect: a)
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0 point to a similar effect: a) I. J. S. Fairlamb, A. R. Kapdi, A. F. Lee, Org. Lett. 2004, 6, 4435-4438;
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Org. Lett.
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Fairlamb, I.J.S.1
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33645887524
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Y. Macé, A. R. Kapdi, I. J. S. Fairlamb, A. Jutand, Organomet al.lics 2006, 25, 1795-1800;
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Macé, Y.1
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I. J. S. Fairlamb, A. R. Kapdi, A. F. Lee, G. P. McGlacken, F. Weissburger, A. H. M. de Vries, L. Schmieder-van de Vondervoort, Chem. Eur. J. 2006, 12, 8750-8761;
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Fairlamb, I.J.S.1
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34
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62149094716
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P. Sehnal, H. Taghzouti, I. J. S. Fairlamb, A. Jutand, A. F. Lee, A. C. Whitwood, Organomet al.lics 2009, 28, 824-829.
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Sehnal, P.1
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Whitwood, A.C.6
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35
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47749119523
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2] complexes have been investigated only scarcely as palladium sources for homogeneous catalysis. For selected recent examples, see: a)
-
2] complexes have been investigated only scarcely as palladium sources for homogeneous catalysis. For selected recent examples, see: a) V. H. Purecha, N. S. Nandurkar, B. M. Bhanage, J. M. Nagarkar, Tetrahedron Lett. 2008, 49, 5252-5254;
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Purecha, V.H.1
Nandurkar, N.S.2
Bhanage, B.M.3
Nagarkar, J.M.4
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37
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77950807434
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dbm = dibenzoylmethanato; bac = benzoylacetonato; tmhd = tetramethylheptanedionato; hfac = hexafluoroacetylacetonato
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dbm = dibenzoylmethanato; bac = benzoylacetonato; tmhd = tetramethylheptanedionato; hfac = hexafluoroacetylacetonato.
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38
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0348012387
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Complexes of the type [(NHC) Pd (R-acac) X] are scarce; for precedents, see: a)
-
Complexes of the type [(NHC) Pd (R-acac) X] are scarce; for precedents, see: a) K. Hiraki, M. Onishi, K. Sugino, J. Organomet. Chem. 1979, 171, C50-C52;
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Hiraki, K.1
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0040004994
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K. Hiraki, K. Sugino, M. Onishi, Bull. Chem. Soc. Jpn. 1980, 53, 1976-1981;
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D. S. McGuinness, M. J. Green, K. J. Cavell, B. W. Skelton, A. H. White, J. Organomet. Chem. 1998, 565, 165-178.
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41
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77950795516
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Despite repeated attempts we were unable to obtain suitable crystals for X-ray analysis of 8
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Despite repeated attempts we were unable to obtain suitable crystals for X-ray analysis of 8.
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-
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42
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77950815806
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This is in sharp contrast with the observation by Cavell and coworkers that [(IDM) Pd (tfac) Me] (IDM = 1, 3-dimethylimidazol-2-ylidene, tfac = trifluoroacetylacetonato) and [(IDM) Pd (hfac) Me] are active precatalysts for the Heck reaction; see reference [15c]
-
This is in sharp contrast with the observation by Cavell and coworkers that [(IDM) Pd (tfac) Me] (IDM = 1, 3-dimethylimidazol-2-ylidene, tfac = trifluoroacetylacetonato) and [(IDM) Pd (hfac) Me] are active precatalysts for the Heck reaction; see reference [15c].
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43
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77950855947
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Such a short catalyst life could be the consequence of high concentration of bare monoligated palladium (0) species, which will aggregate and precipitate. We are currently investigating, among others, this hypothesis
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Such a short catalyst life could be the consequence of high concentration of bare monoligated palladium (0) species, which will aggregate and precipitate. We are currently investigating, among others, this hypothesis.
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44
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0000766319
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For examples of O, O-to C-bound rearrangement of β-diketonato palladium (II) species, see: a)
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For examples of O, O-to C-bound rearrangement of β-diketonato palladium (II) species, see: a) S. Baba, T. Ogura, S. Kawaguchi, Bull. Chem. Soc. Jpn. 1974, 47, 665-668;
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43649086728
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See also ref. 9 a
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V. S. Tkach, D. S. Suslov, G. Myagmarsuren, G. V. Ratovskii, A. V. Rohin, T. Felix, F. K. Shmidt, J. Organomet. Chem. 2008, 693, 2069-2073. See also ref. 9 a.
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Tkach, V.S.1
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51
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41249099041
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C-O reductive elimination from T-shaped palladium (II) complexes is known; see
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C-O reductive elimination from T-shaped palladium (II) complexes is known; see: J. P. Stambuli, Z. Weng, C. D. Incarvito, J. F. Hartwig, Angew. Chem. 2007, 119, 7818-7821;
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Stambuli, J.P.1
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Angew. Chem. Int. Ed. 2007, 46, 7674-7677.
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53
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77950838891
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0] (m/z 494.2)
-
0] (m/z 494.2) ;
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-
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55
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0033403533
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For synthesis of carbenes, see:, and references therein
-
For synthesis of carbenes, see: A. J. Arduengo, III., J. C. Calabrese, F. Davidson, H. V. Rasika Dias, J. R. Goerlich, R. Krafczyk, W. J. Marshall, M. Tamm, R. Schmutzler, Helv. Chim. Acta 1999, 82, 2348-2364, and references therein.
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Arduengo, A.J.I.1
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Krafczyk, R.6
Marshall, W.J.7
Tamm, M.8
Schmutzler, R.9
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