Cyclopropenes for the Stepwise Synthesis of 1,2,4,5-Tetraarylbenzenes via 1,4-Cyclohexadienes

This paper describes a synthetic approach to the synthesis of 1,2,4,5-tetraarylbenzene derivatives from cyclopropenes. The Lewis acid-mediated dimerization of cyclopropenes gives tricyclo[3.1.0.02,4]hexane derivatives. The subsequent thermal ring-opening reaction under solvent-free conditions gives 1,4cyclohexadienes bearing quaternary carbons. The novel Br2- mediated oxidative rearrangement of 1,4-cyclohexadienes takes place to give 1,2,4,5-tetraarylbenzene derivatives in high to excellent yields.

Automated summary

This paper presents a synthetic method for the synthesis of 1,2,4,5-tetraarylbenzene derivatives using cyclopropenes as starting materials. Through Lewis acid-mediated dimerization, cyclopropenes are transformed into tricyclo[3.1.0.02,4]hexane derivatives. The subsequent thermal ring-opening reaction under solvent-free conditions yields 1,4-cyclohexadienes bearing quaternary carbons. The novel Br2-mediated oxidative rearrangement of 1,4-cyclohexadienes results in the formation of 1,2,4,5-tetraarylbenzene derivatives with high to excellent yields.