Heck Reaction Boosted Heterocycle Ring-Closing and Ring-Opening Rearrangement: A Strategy for the Synthesis of Indolyl-Type Ligands.

Abstract

A novel method for P-involved heterocycle ring-closing-ring-opening rearrangement (HRR) via the Heck reaction is disclosed. The approach enables direct installation of a phosphorus-containing aryl group onto the C2 position of indole. This new rearrangement directly transforms easily prepared indole derivatives into indolyl-derived phosphonates and phosphinic acids with high yields, and many of the products are difficult to obtain by using established methods. This new HRR reaction provides an extremely simple and step-economic method to induce C-C bond formation and P-N bond cleavage for the synthesis of a variety of indolyl-type ligands.