[3,3]-Rearrangements of N-Oxyindoles

Abstract

The concerted Ag-catalyzed rearrangement of N-indolyl carbonates and esters to afford 3-oxyindole derivatives with broad functional-group compatibility is presented. In addition, this concerted [3,3]-rearrangement approach was expanded to the synthesis of phosphonate and sulfonamide derivatives without the use of an Ag catalyst. Control experiments suggested that no radical pathway is involved at any stage of the rearrangement process.