Journal
TETRAHEDRON LETTERS
Volume 55, Issue 49, Pages 6647-6651Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.10.068
Keywords
Acylation; Phenanthridine; Minisci reaction; Photochemistry; fac-Ir(ppy)(3)
Categories
Funding
- Natural Science Foundation of China [31402109]
- Natural Science Foundation of Hunan Province [13JJ5044]
- Research Fund for the Doctoral Program of Higher Education, Ministry of Education of China [20124320120006]
- Important Science & Technology Specific Projects of Hunan Province [2012FJ1004]
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In this study, a new type of Minisci reaction for regiospecific acylation of phenanthridine has been developed based on cross dehydrogenative coupling (CDC) strategy. Using substoichiometric amount of TBAB (tetrabutylammonium bromide, 30 mol %) and K2S2O8 as an oxidant, acyl radicals generate from aldehyde substrates under thermal conditions followed by a regiospecific intermolecular acylation with phenanthridine. Furthermore, a preliminary research has indicated that the acylation reaction can be carried out at room temperature when K2S2O8/TBAB is displaced by (NH4)(2)S2O8 and another 5 mol % of fac-Ir(ppy)(3) is used as photocatalyst under irradiation of visible light. This intermolecular acylation reaction provides an easy access to 6-acylated phenanthridine derivatives. (C) 2014 Elsevier Ltd. All rights reserved.
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