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0342394939
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note
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We attempted to prepare the corresponding imine from 1 and benzylamine. However, the imine was thermally unstable and was not tolerated by the palladium-catalyzed reaction.
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For lithiation of dimethylaminomethylferrocene at the 2-position with n-butyllithium, see D. W. Slocum, B. W. Rockett, C. R. Hauser, J. Am. Chem. Soc. 1965, 87, 1241-1246. We used tert-butyllithium to obtain a higher yield of 3.
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note
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3 also gave a trace of the desired product 4e.
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We assume that intramolecular binding of the nitrogen atom of the imino group to the aryl(chloro)palladium complex facilitates deprotonation of the resulting complex to give I. Miura et al. recently reported the synthesis of benzofurans by means of a palladium-catalyzed intramolecular C O bond formation: Y. Terao, T. Satoh, M. Miura, M. Nomura, Bull. Chem. Soc. Jpn. 1999, 72, 2345-2350.
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0001012389
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(2,6-dichlorophenyl)propionaldehyde was prepared from 2,6-dichlorobenzyl chloride and N-cyclohexyliminoacetaldehyde in diethyl ether. For the lithiation of N-cyclohexyliminoacetaldehyde with lithium diisopropylamide, see G. Wiltig, A. Hesse, Org. Synth. Coll. Vol. 6, 1988, 901-904.
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Org3
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