Metal-Free Domino One-Pot Decarboxylative Cyclization of Cinnamic Acid Esters: Synthesis of Functionalized Indanes

Trifluoroacetic acid promoted unprecedented domino reaction for the synthesis of diverse indanes starting from simple cinnamic acid esters is described. Their formation can be explained via acid triggered decarboxylation of cinnamic acid esters and subsequent inter/intramolecular cyclization. Overal...

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Veröffentlicht in:Journal of organic chemistry 2016-12, Vol.81 (24), p.12212-12222
Hauptverfasser: Gopi Krishna Reddy, Alavala, Satyanarayana, Gedu
Format: Artikel
Sprache:eng
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Zusammenfassung:Trifluoroacetic acid promoted unprecedented domino reaction for the synthesis of diverse indanes starting from simple cinnamic acid esters is described. Their formation can be explained via acid triggered decarboxylation of cinnamic acid esters and subsequent inter/intramolecular cyclization. Overall process involves in the intramolecular cleavage of two σ-bonds (C–O and C–C) and inter/intramolecular construction of two/one C–C σ-bond(s). Significantly, this protocol was successful without the aid of any metal salts.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.6b02015