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For a recent example see
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For a recent example see: Frohn, M.; Burli, R. W.; Riahi, B.; Hungate, R. W. Tetrahedron Lett. 2007, 48, 487-489.
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(b) Liu, T.-Y.; Long, J.; Li, B.-J.; Jiang, L.; Li, R.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. Org. Biomol. Chem. 2006, 4, 2097-2099.
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0034803619
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For Pd-catalyzed reactions, see: a
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For Pd-catalyzed reactions, see: (a) Stauffer, S. R.; Beare, N. A.; Stambuli, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4641-4642.
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(d) You, J.; Verkade, J. G. Angew. Chem., Int. Ed. 2003, 42, 5051-5053.
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Verkade, J.G.2
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(f) Uno, M.; Seto, K.; Ueda, W.; Masuda, M.; Takahashi, S. Synthesis 1985, 506-508.
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Uno, M.1
Seto, K.2
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Takahashi, S.5
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12
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0027731073
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For Cu-catalyzed reactions, see: a
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For Cu-catalyzed reactions, see: (a) Okuro, K.; Furuune, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 7606-7607.
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Okuro, K.1
Furuune, M.2
Miura, M.3
Nomura, M.4
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(b) Pivsa-Art, S.; Fukui, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1996, 69, 2039-2042.
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Fukui, Y.2
Miura, M.3
Nomura, M.4
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14
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(c) Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Chem. Eur. J. 2004, 10, 5607-5622.
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Cristau, H.-J.1
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Taillefer, M.4
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16
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39349115803
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3N ligand is a viscous and air-sensitive liquid. The bench-top handling of this ligand in air for screening and scale-up was found to be somewhat unattractive for our needs. See refs 4d,e.
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3N ligand is a viscous and air-sensitive liquid. The bench-top handling of this ligand in air for screening and scale-up was found to be somewhat unattractive for our needs. See refs 4d,e.
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17
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0042912889
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DPPF has been previously examined in related cross-coupling reactions, see: a
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DPPF has been previously examined in related cross-coupling reactions, see: (a) Gao, C.; Tao, X.; Qian, Y.; Huang, J. Synlett 2003, 1716-1718.
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Synlett
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Gao, C.1
Tao, X.2
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18
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(b) Mitin, A. V.; Kashin, A. N.; Beletskaya, I. P. Russ. J. Org. Chem. 2004, 40, 802-812.
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Mitin, A.V.1
Kashin, A.N.2
Beletskaya, I.P.3
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19
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39349084404
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When 1.2 equiv of KOtBu was used, incomplete conversion of 3 was observed.
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When 1.2 equiv of KOtBu was used, incomplete conversion of 3 was observed.
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20
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0037694384
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Allyl groups are susceptible to palladium-catalyzed olefin isomerizations under certain conditions, see
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Allyl groups are susceptible to palladium-catalyzed olefin isomerizations under certain conditions, see: Negishi, E.-I. Handb. Organopalladium Chem. Org. Synth. 2002, 2, 2783-2788.
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Negishi, E.-I.1
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21
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39349084220
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Use of MeI as an in situ trapping reagent has been demonstrated by Hartwig et al. in the palladium-catalyzed arylation of malonates but not cyanoacetates, see ref 4b. No other alkylating reagents have been demonstrated as in situ traps
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Use of MeI as an in situ trapping reagent has been demonstrated by Hartwig et al. in the palladium-catalyzed arylation of malonates but not cyanoacetates, see ref 4b. No other alkylating reagents have been demonstrated as in situ traps.
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22
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39349098881
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In the absence of a Pd catalyst/ligand, the control experiment of 5-bromopyrimidine with 3 and KOt-Bu produced ∼30% conversion after overnight heating, whereas 3-bromopyridine gave no detectable amount of product, indicating efficiency of Pd catalysis
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In the absence of a Pd catalyst/ligand, the control experiment of 5-bromopyrimidine with 3 and KOt-Bu produced ∼30% conversion after overnight heating, whereas 3-bromopyridine gave no detectable amount of product, indicating efficiency of Pd catalysis.
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23
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14844330054
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(a) Shen, Q.; Shekhar, S.; Stambuli, J. P.; Hartwig, J. F. Angew. Chem., Int. Ed. 2005, 44, 1371-1375.
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Shen, Q.1
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Stambuli, J.P.3
Hartwig, J.F.4
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