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Synthesis 2012; 44(15): 2374-2384
DOI: 10.1055/s-0032-1316542
DOI: 10.1055/s-0032-1316542
paper
Copper(II)-Mediated Cascade Oxidative C–C Coupling and Aromatization: Synthesis of 3-Hydroxyphenanthridinone Derivatives
Further Information
Publication History
Received: 23 March 2012
Accepted after revision: 15 May 2012
Publication Date:
29 June 2012 (online)
Abstract
A novel copper(II) acetate mediated synthesis of 3-hydroxyphenanthridin-6(5H)-ones from N-(3-oxocyclohex-1-enyl)benzamides was developed. The process is postulated to involve an intramolecular oxidative C(sp2)–C(sp3) bond formation followed by dehydrogenative aromatization.
Key words
copper(II) acetate - phenanthridinone - C–H functionalization - C–C oxidative coupling - dehydrogenative aromatizationSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
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For recent reviews on C–C bond formation, see:
For selected examples on C–C cross-coupling, see:
For selected examples, see:
For selected examples, see:
For selected examples on the synthesis of phenanthridinones by Pd(OAc)2, see:
For the synthesis of substrate, see:
For some examples on the use of Cu(OAc)2, see: