Synlett 2010(2): 281-285  
DOI: 10.1055/s-0029-1219169
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© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Synthesis of Allenyl Perfluoroalkyl Ketones from Mono-1,2-Addition-Elimination Reaction of Allenoates with RfMgX

Guangke He, Can Xue, Chunling Fu, Shengming Ma*
Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, P. R. of China
Fax: +86(21)62609305; e-Mail: masm@mail.sioc.ac.cn;
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Publikationsverlauf

Received 7 August 2009
Publikationsdatum:
04. Januar 2010 (online)

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Abstract

An efficient method for the synthesis of perfluoroalkyl allenyl ketones via the 1,2-addition-elimination reaction of per­fluoroalkyl Grignard reagents with allenoates has been established. No further reaction was observed between these perfluoroalkyl ketones and RfMgX. Under the catalysis of PdCl2 or AuCl3, perfluoroalkyl 1,2-allenyl ketones can be transformed to 2-perfluoroalkyl-substituted furans; they may also undergo 1,2-addition with organolithiums to afford tertiary 1,2-allenols containing a perfluoroalkyl group.