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note
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e) The best previous results for this reaction are described in ref. [2c], although no yield of isolated product is reported.
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note
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The half-life was determined by GC analysis.
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While exceedingly high turnover numbers have been realized for the coupling of phenyl boronic acid with 4-bromoacetophenone, this is a particularly trivial process and does not extend to the efficient coupling of unactivated and ortho-substituted substrates at low catalyst levels. We have previously shown this reaction to proceed even in the absence of added ligand and recommend that it not be used as a benchmark to test new catalysts, see ref. [7a].
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For a recent report describing the cross-coupling of aryl chlorides with alkyl boronic acids, see: N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553. For a report describing the coupling of an alkyl boronic acid with an alkyl bromide, see: J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 13662.
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note
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II palladate species.[14a] While we cannot unequivocally rule this out, the fact that higher levels of catalytic activity for analogous C-N couplings have been observed for catalysts derived from 2-dicyclohexylphosphanyl-2′,4′,6′- triisopropylbiphenyl than for 1 (E. R. Stricter, S. L. Buchwald, unpublished results) cast doubt on this explanation of the high level of catalytic activity manifested with 1.
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