Abstract
AbstractHalofunctionalization of various unactivated arylalkynes to the corresponding 1H‐indenes in the presence of a particular class of carboxaldehydes and boron trihalides (BX3, X=F, Cl, Br, I) is described. A diverse array of halofunctionalized indenes substituted with a heterocycle has been synthesized regioselectively with BX3 as a promotor for the carbocyclization and a source of X− for halogenation. This reaction proceeds via a formal halogenative [4+1] cycloaddition between arylalkynes and carboxaldehydes promoted by boron trihalides to generate halofunctionalized indenes. The usefulness of the halofunctionalized indenes was demonstrated by their conversion to other derivatives via coupling, nucleophilic substitution, and oxidation.magnified image
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