Reaction of 1,8-diiodo- or 1,8-dibromonaphthalene with a mixture of Ni(COD) 2 and trimethylphosphine gives the oxidative addition product Ni(PMe 3 ) 2 (X)(C 10 H 6 X) (X = Br, I), which on reduction with Na/Hg gives perylene or, in the presence of alkynes, 1,2-disubstituted acenaphthylenes.
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Brown et al. (2003) studied this question.
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