Journal
TETRAHEDRON LETTERS
Volume 52, Issue 44, Pages 5847-5850Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.08.146
Keywords
Arynes; N-Arylation; Acetanilides; ortho-Silylaryl triflates; Tetrabutylammonium; triphenyldifluorosilicate
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An efficient, mild and transition-metal-free method for the N-arylation of acetanilides, leading to a range of unsymmetrical diarylamine products is reported. Reactions of ortho-silylaryl triflates with acetanilides in the presence of tetrabutylammonium triphenyldifluorosilicate (TBAT) in toluene afforded the desired products in good to excellent yields. Regioselectivity was also observed when unsymmetrical aryne precursors were used. (C) 2011 Elsevier Ltd. All rights reserved.
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