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According to the Strem catalog, 2004-2006, the 2-(di-tert-butylphosphino) -biphenyl and the 2-di-tert-butylphosphino-2′-methyl-biphenyl cost respectively $19.7/mmol and $33.8/mmol when purchased by 500 mg. Palladium-(II) dichloride and palladium(II) acetate cost respectively $6.7/mmol and $11.7/mmol when purchased by 1 g.
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note
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(IPr)Pd(allyl)Cl (3) is commercially available from Strem Chemicals for small quantities (hundreds of mg) and from Umicore AG for larger quantities.
-
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65
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33645458001
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note
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As a testimony to their stability, samples of 7 and 8 retrieved from our laboratories in New Orleans showed no decomposition after being subjected for 2 months to harsh environmental conditions (90/95 °F, high humidity and high level of volatile chemicals) imposed by Hurricane Katrina.
-
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66
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33645460164
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note
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Owing to the slightly lower quality of structural data for (IPr)Pd(crotyl)-Cl, 5, (despite repeated attempts) higher error factors preclude a bond length discussion involving 5; it is of note that an increase of the dissymmetry of the allyl moiety is observed with increased steric substitution at the allylic terminal position.
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67
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33645454059
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note
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allyl.
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33645459911
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note
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Prof. Irina P. Beletskaya (Moscow State University) kindly pointed out reduction of Pd(II) to Pd(0) by the boronic acid as another plausible activation pathway for our complexes in the case of the Suzuki-Miyaura reaction. Although we have carried out experiments to examine whether the two mentioned mechanisms occur for the activation of 3a (ref 23a) and we can presume the same mechanism to be at play for 5-8, however, we cannot totally rule out reduction by the boronic acid for these new complexes. Experiments addressing this possibility are currently ongoing.
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70
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note
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According to the Aldrich catalog 2004-2005, cinnamyl chloride (by 100 g) and prenyl chloride (by 25 g) cost respectively $94.2/mol and $398.7/mol.
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According to the Acros catalog 2004-2005, 1-chloronaphthalene and 1-bromonaphthalene, when purchased by 100 mL quantities, cost respectively $28.9/mol and $57.6/mol.
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For complementary characterization of this compound, see ref 53.
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