Efficient Diels–Alder Reaction of 1,2-Benzoquinones with Arynes and Its Utility in One-Pot Reactions
- 10 December 2012
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 14 (24), 6238-6241
- https://doi.org/10.1021/ol302997q
Abstract
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.Keywords
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