Efficient Diels–Alder Reaction of 1,2-Benzoquinones with Arynes and Its Utility in One-Pot Reactions
作者:Trinadh Kaicharla、Sachin Suresh Bhojgude、Akkattu T. Biju
DOI:10.1021/ol302997q
日期:2012.12.21
A new protocol for the efficient Diels-Alder reaction of 1,2-benzoquinones with arynes is reported. The aryne generated by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes a facile Diels-Alder reaction with 1,2-benzoquinones, affording the dioxobenzobicyclooctadienes in moderate to excellent yields. In addition, this methodology has been applied to the one-pot synthesis of benzoquinoxalinobarrelene and naphthalene derivatives.