Dearomatization of C6 Aromatic Hydrocarbons by Main Group Complexes

Abstract

The dearomatization reaction is a powerful method for transformation of simple aromatic compounds to unique chemical architectures rapidly in synthetic chemistry. Over the past decades, the chemistry in this field has evolved significantly and various important organic compounds such as crucial bioactive molecules have been synthesized through dearomatization. In general, photochemical conditions or assistance by transition metals are required for dearomatization of rigid arenes. Recently, main-group elements, especially naturally abundant elements in the Earth's crust, have attracted attention as they have low toxicity and are cost-effective compared to the late transition metals. In recent decades, a variety of low-valent main-group molecules, which enable the activation of stable aromatic compounds under mild conditions, have been developed. This minireview highlights the developments in the chemistry of dearomatization of C₆ aromatic hydrocarbons by main-group compounds leading to the formation of seven-membered EC₆ (E=main-group elements) ring or cycloaddition products.

Keywords: Büchner ring expansion reaction; aromatic C6 hydrocarbon; cycloaddition; dearomatization; low-valent main-group elements.