Efficient diels-alder reaction of 1,2-benzoquinones with arynes and its utility in one-pot reactions

TitleEfficient diels-alder reaction of 1,2-benzoquinones with arynes and its utility in one-pot reactions
Publication TypeJournal Article
Year of Publication2012
AuthorsKaicharla, T, Bhojgude, SSuresh, Biju, AT
JournalOrganic Letters
Volume14
Issue24
Pagination6238–6241
Date PublishedDEC
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.

DOI10.1021/ol302997q
Funding Agency

Council of Scientific & Industrial Research (CSIR) - India

Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

6.142

Divison category: 
Organic Chemistry