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Tuning the regioselectivity of the Pd-catalyzed coupling reaction of propargylic mesylates and (Z)-2-ethoxycarbonylethenyl zinc iodide or PhZnBr is acheived by subtle choice of the ligand. When PPh3 is the ligand, alkynes are formed, whereas when 2-diphenylphosphanyl-2′-hydroxy-1,1′-binaphthalene is the ligand, allenes are formed.
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Ma et al. (2003) studied this question.
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