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Issue 34, 2014
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An expedient route to heterocycles through α-arylation of ketones and arylamides by microwave induced thermal SRN1 reactions

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Abstract

Microwave irradiation promotes a quick aromatic nucleophilic substitution by a thermally induced electron transfer process to form new C–C bonds by the coupling of aryl radicals and enolate nucleophiles. Diverse 2-aryl-1-phenylethanones can be prepared by the direct α-arylation of acetophenone with different haloarenes. The ketone enolate anion is generated by deprotonation with tBuOK in DMSO and the reaction is carried out in a closed microwave vessel at 70–100 °C for 10 min. This simple procedure also allows the synthesis of deoxybenzoin and indole heterocycle derivatives by inter- or intra-molecular ring closure reactions, with moderate to excellent substitution yields.

Graphical abstract: An expedient route to heterocycles through α-arylation of ketones and arylamides by microwave induced thermal SRN1 reactions

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Publication details

The article was received on 06 Jan 2014, accepted on 25 Mar 2014 and first published on 01 Apr 2014


Article type: Paper
DOI: 10.1039/C4RA00120F
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RSC Adv., 2014,4, 17490-17497

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    An expedient route to heterocycles through α-arylation of ketones and arylamides by microwave induced thermal SRN1 reactions

    S. M. Soria-Castro, D. A. Caminos and A. B. Peñéñory, RSC Adv., 2014, 4, 17490
    DOI: 10.1039/C4RA00120F

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