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Reactions with terminal alkynes such as 1-hexyne, phenylacetylene, and trimethylsilylacetylene afforded the corresponding fluoroarenes, albeit in 5%, 3%, and 5% yields (determined by 19F NMR spectroscopy with PhCF3 as an internal standard), respectively
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A stepwise oxidative cyclization model satisfactorily illustrates the experimental results. This stepwise model consists of (i) rapid pre-equilibrium between the reactants (Ni0 and 1) and the intermediary nickelacyclopropane (see ref. [9]) and (ii) subsequent slow insertion of 2 into the nickelacyclopropane. For details, see the Supporting Information
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A stepwise oxidative cyclization model satisfactorily illustrates the experimental results. This stepwise model consists of (i) rapid pre-equilibrium between the reactants (Ni0 and 1) and the intermediary nickelacyclopropane (see ref. [9]) and (ii) subsequent slow insertion of 2 into the nickelacyclopropane. For details, see the Supporting Information.
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In the case of the reaction of 1,1-difluoro-1,6-enyne 5 with diphenylacetylene (2a), β-hydrogen elimination yielding the corresponding fluoroarene 6 was sluggish, probably due to the rigid bicyclic system of the intermediate. Thus, in the presence of the reductant, Et3B-iPrOLi, transmetalation from the intermediary cyclohexadienylnickel(II) fluoride corresponding to C in Scheme 2 preferably occurred rather than β-hydrogen elimination, leading to the cyclohexadiene. To avoid confusion, we herein demonstrate that the stoichiometric reaction, conducted in the absence of the reductant, selectively afforded the corresponding fluoroarene 6 [Eq. (1)]
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Since generation of ethylene and dihydrogen during the reaction was confirmed by each gas detector, a β-hydrogen elimination-reductive elimination sequence definitely occurred as a route from NiII to Ni0
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