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Synfacts 2010(9): 1008-1008  
DOI: 10.1055/s-0030-1257920
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Diarylsquaramides Selectively from Squareate Esters

Contributor(s): Timothy M. Swager, Stefanie A. Sydlik
A. Rostami, A. Colin, X. Y. Li, M. G. Chudzinski, A. J. Lough, M. S. Taylor*
University of Toronto, Canada
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Publikationsdatum:
23. August 2010 (online)

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Significance

Symmetric and asymmetric diaryl­squaramides were synthesized in good to excellent yields (80-99%). Since this reaction is slower than that with alkyl amines, traditional conditions result in a sluggish reaction and/or a significant amount of squaraine isomers as an undesired byproduct. This work is the first to successfully control the squaraine byproduct formation and speed by selecting an appropriate Lewis acid ­catalyst.