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An open-and-shut strategy: preparation of benzo-fused indanes by ring-opening of a vinylogous acyl triflate and metal-catalyzed Asao–Yamamoto benzannulation

An open-and-shut strategy: preparation of benzo-fused indanes by ring-opening of a vinylogous acyl triflate and metal-catalyzed Asao–Yamamoto benzannulation

Authors :
Jones, David M.
Dudley, Gregory B.
Source :
Tetrahedron. Jun2010, Vol. 66 Issue 26, p4860-4866. 7p.
Publication Year :
2010

Abstract

Abstract: A two-step strategy for the synthesis of benzo-fused indanes is outlined herein. The strategy draws on two independent methodologies: the tandem addition/fragmentation of vinylogous acyl triflates (VATs) and the intramolecular benzannulation of o-alkynylphenyl ketones. Reduction of this strategy to practice involves the use of aryltriazenes as masked aryl iodides; a synthetic equivalent of 2-iodophenyllithium is featured. Benzo-fused indanes are prepared efficiently and in high yield. [Copyright &y& Elsevier]

Details

Language :
English
ISSN :
00404020
Volume :
66
Issue :
26
Database :
Academic Search Index
Journal :
Tetrahedron
Publication Type :
Academic Journal
Accession number :
51421959
Full Text :
https://doi.org/10.1016/j.tet.2010.03.014