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4-Penten-1-ols 1 react, irrespective of their pattern of substitution (R1-R3 = H, Me, Ph), with tri-n-butyl-(p-methoxyphenyl)stannane and CuCl2 in the presence of catalytic amounts of bis(benzonitrile)palladium(II) chloride to give exclusively 2-(p-methoxyphenyl)tetrahydropyrans 2. In contrast, 1,1-difunctionalized compounds (2 and 3) and 1,3-difunctionalized compounds (4) are generally obtained with tri-n-butyl(phenyl)stannane. The related Heck reaction only results in 1,2-arylchlorination.
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Tamaru et al. (1986) studied this question.
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