Hypervalent iodine compounds have been widely used as oxidants in organic reactions due to their unique reactivity and environmentally friendly properties. In this presentation, we have outlined a novel atom-efficient hypervalent iodine (III) chemistry involving reductive iodonio-Claisen rearrangement (RICR). It was found that a mixture of hypervalent iodine (III) compounds and allyltrimethylsilane in presence of borontrifluoride etherate underwent RICR to afford ortho-allyl iodoarenes in synthetically useful to good yields. An electron donating group at meta position was required to favor the RICR over reductive elimination. The ortho-allyliodoarenes can be further functionalized to synthetically valuable benzofurans, dihydrobenzofurans, dihydrobenzopyrans, indolines and related molecules.

Synthesis of <i>ortho</i>-allyliodoarenes employing reductive iodonio-claisen rearrangement

244th National Meeting (2012)

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Synthesis of ortho-allyliodoarenes employing reductive iodonio-claisen rearrangement