High pressure promoted dearomatization of nitroarenes by [4+2] cycloadditions with silyloxydienes

Simple nitroarenes such as nitronaphthalenes and nitroquinolines smoothly undergo dearomatizing [4+2] cycloadditions with silyloxydienes under 16 kbar. Highly functionalized 3-dimensional polycyclic adducts bearing a tetrasubstituted carbon centre at the ring junction are obtained in one step from simple raw materials. This unprecedented dearomative Diels-Alder process is performed at room temperature without any chemical promoter, illustrating the exceptional role of high pressure as a physical promoter.

Automated summary

This article investigates the reaction of nitroarenes with silyloxydienes under high pressure and demonstrates the successful dearomatizing [4+2] cycloadditions at room temperature, resulting in highly functionalized compounds with tetrasubstituted carbon centers.