A novel synthesis of benzocyclobutenones
TL;DR: In this paper, the authors proposed a simple and efficient route to benzocyclobutenones using the lithium-iodine exchange initiated cyclization of o-iodo-n-methoxy-N-methyl phenylacetamides.
About: This article is published in Tetrahedron Letters.The article was published on 1992-09-08. It has received 48 citations till now. The article focuses on the topics: Ketone.
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TL;DR: In this article, the authors present a review of N-METHOXY-N-mETHYLAMIDES applications in synthamesis and apply it to organic preparation and procedures.
169 citations
160 citations
TL;DR: These investigations provide a distinct way to prepare chiral carbon frameworks that are nontrivial to access with conventional methods.
Abstract: Here we report the first highly enantioselective Rh-catalyzed carboacylation of olefins via C–C bond activation of benzocyclobutenones. Good yields and excellent enantioselectivities (92–99% ee, 14 examples) were obtained for substrates with various steric and electronic properties. In addition, fully saturated poly-fused rings were prepared from the carboacylation products through a challenging catalytic reductive dearomatization approach. These investigations provide a distinct way to prepare chiral carbon frameworks that are nontrivial to access with conventional methods.
156 citations
TL;DR: In this article, a review of aspects related to the synthesis, reactions and applications of benzocyclobutenes is presented, including reactions, reactions, and applications, as well as the synthesis process.
127 citations
TL;DR: A new catalyst system for the intramolecular acylation of aldehydes with aryl bromides via C-H functionalization is described, which allows for the synthesis of a wide variety of highly functionalized benzocyclobutenones with a diverse set of substitution patterns from simple and easily accessible precursors.
Abstract: A new catalyst system for the intramolecular acylation of aldehydes with aryl bromides via C−H functionalization is described. The transformation is distinguished by a remarkable functional group tolerance and hence allows for the synthesis of a wide variety of highly functionalized benzocyclobutenones with a diverse set of substitution patterns from simple and easily accessible precursors.
108 citations
References
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TL;DR: Readily preparable N-methoxy-N-methylamides couple in good yields with Grignard and organolithium reagents to produce ketones, and are reduced with hydrides to afford aldehydes.
1,611 citations
TL;DR: This paper showed that o-(α-phenylthio)alkylbenzoyltrimethylsilanes with a suitable catalyst such as Group 6 metal carbonyls in refluxing toluene or dioxane afforded benzocyclobutenones.
13 citations
TL;DR: Halogen metal exchange, occuring in presence of electrophilic centres, provides a simple and efficient route to 1-aryl-benzocyclobutenols and benzocyclOButenes.
12 citations