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Synfacts 2014; 10(1): 0040
DOI: 10.1055/s-0033-1340385
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Superacid Anions from Tetracyanothiophene

Contributor(s):
Timothy M. Swager
,
Jonathan G. Weis
Sakai T, * Seo S, Matsuoka J, Mori Y. * Meijo University, Nagoya, Japan
Synthesis of Functionalized Tetracyanocyclopentadienides from Tetracyanothiophene and Sulfones.

J. Org. Chem. 2013;
78: 10978-10985
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Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

desulfurization - organic salts - sulfones - superacids - thiophenes

Significance

The authors report an improved synthesis of tetracyanocyclopentadienyl anions, a class of superacid anions with functional handles. By including the leaving group on the nucleophile, product 3 is accessed more directly from thiophene 1 and sulfone 2. The researchers demonstrate the reaction’s utility with a variety of sulfones and successful exchange of cations.


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Comment

Optimization of the reaction conditions revealed a strong dependence on base, with NaH outperforming alkoxide, silazide, and non-ionic nitrogen bases. Using phenylsulfones as the leaving groups proved more facile than using halides. Ketones could not be directly synthesized with this method but can be obtained from the Weinreb amide derivative 3c.


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