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Abstract
Treatment of o-bromoiodobenzene successiveiy with a vinyl Grignard reagent (2+ equivatents) and an allylic hatide (1+ equivalent) gives a good yield of arene containing adjacent vinyl and allyl sidechains.
In recent papers we showed that vinyl or vinylsilyl Grignard reagents can be used to generate and trap arynes from polyhaloarenes.2 The reaction, illustrated below for o-bromoiodobenzene, involves three steps: Grignard exchange, aryne formation, and nucteophilic addition of a second equivalent of Grignard reagent to the aryne.