RECENT APPLICATIONS OF ARYNE CHEMISTRY TO ORGANIC SYNTHESIS. A REVIEW

摘要

Arynes are neutral intermediates in which two adjacent atoms of an aromatic ring lack substituents, thus leaving two atomic orbitals (perpendicular to the aromatic π system) to form a weakly bonding molecular orbital occupied by two electrons. This review is intended to be an update of ortho-benzyne (1,2-di-dehydrobenzene) chemistry and of its derivatives (referred as arynes) published in the last five years (2002-2007), since early work has already been reviewed extensively. The focus of this review is on the application of arynes in organic synthesis, but not on other related aspects such as their generation and capture through the deployment of organometallic complexes, their structures, or the related systems meta-, and para-arynes. Nevertheless, the review will give an overview of general aspects about the structure, reactivity, and the main methods for the generation of arynes. The rest of the article will be devoted to the more recent advances in the synthetic applications of these intermediates.