Synthesis of Indolyl-Tethered Spiro[cyclobutane-1,1'-indenes] through Cascade Reactions of 1-(Pyridin-2-yl)-1H-indoles with Alkynyl Cyclobutanols.

Presented herein is an efficient and unprecedented synthesis of indolyl-tethered spiro[cyclobutane-1,1'-indenes] through the cascade reaction of 1-(pyridin-2-yl)-1H-indoles with alkynyl cyclobutanols. Mechanistic experiments implicate a sequential process in which 1-(pyridin-2-yl)-1H-indole first undergoes an alkenylation with alkynyl cyclobutanol followed by an intramolecular Friedel-Crafts reaction to give the title products. The utility of this novel protocol was reflected by the ample substrate scope, high chemo- and regioselectivity, removable directing group, and scalable preparation. In addition, the product thus obtained can be further derivatized quite efficiently.