Two-directional annelation: Dual benzyne cycloadditions starting from bis(sulfonyloxy)diiodobenzene

Abstract

(Chemical Equation Presented) Double up: Dual cycloadditions of benzynes are demonstrated from bis(sulfonyloxy)diiodobenzene I, which can be viewed as a synthetic equivalent of 3-alkoxy-1,4-benzdiyne II. Importantly, selective halogen-lithium exchange of I enables the tandem generation of benzynes and dual cycloadditions with arynophiles 1 and 2, thus allowing the rapid construction of various highly functionalized bis-cycloadducts. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.