A facile N-arylation of acetanilides with arynes

…, MA Lynch, SL Spring, AD Pechulis, J Raker, Y Wang

Index: Haber, James C.; Lynch, Michael A.; Spring, Stacey L.; Pechulis, Anthony D.; Raker, Joseph; Wang, Yi Tetrahedron Letters, 2011 , vol. 52, # 44 p. 5847 - 5850

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Citation Number: 10

Abstract

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.

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