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α-Arylation by Rearrangement: On the Reaction of Enolates with Diaryliodonium Salts

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Abstract

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Surprising equilibration: A new mechanism for the title reaction is supported by DFT calculations and experimental observations. The C[BOND]I and O[BOND]I intermediates are isoenergetic and equilibrate quickly. Thus, any chiral information induced in the initial complex will be destroyed. In the final C[BOND]C bond-forming step, a [2,3]-rearrangement from the O[BOND]I bonded intermediate is slightly preferred over the [1,2]-elimination from the C[BOND]I bonded isomer (see scheme).

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