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Synthesis 2013; 45(5): 609-614
DOI: 10.1055/s-0032-1316855
paper
© Georg Thieme Verlag Stuttgart · New York

Iron(III)-Catalyzed Dehydration C(sp2)–C(sp2) Coupling of Tertiary Pro­pargyl Alcohols and α-Oxo Ketene Dithioacetals: A New Route to gem-Bis(alkylthio)-Substituted Vinylallenes

Qian Li
a   College of Chemistry and Chemical Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang 212013, P. R. of China
,
Yeming Wang
c   Key Laboratory of Preparation and Applications of Environmental Friendly Materials (Jilin Normal University), Chinese Ministry of Education, Siping 136000, P. R. of China
,
Zhongxue Fang
b   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China
,
Peiqiu Liao
b   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China
,
Badru-Deen Barry
b   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China
,
Guangbo Che*
a   College of Chemistry and Chemical Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang 212013, P. R. of China
c   Key Laboratory of Preparation and Applications of Environmental Friendly Materials (Jilin Normal University), Chinese Ministry of Education, Siping 136000, P. R. of China
,
Xihe Bi*
b   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China
c   Key Laboratory of Preparation and Applications of Environmental Friendly Materials (Jilin Normal University), Chinese Ministry of Education, Siping 136000, P. R. of China
d   State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Fax: +86(431)85099759   eMail: bixh507@nenu.edu.cn   eMail: guangbochejl@yahoo.com
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Publikationsverlauf

Received: 09. Januar 2013

Accepted after revision: 23. Januar 2013

Publikationsdatum:
06. Februar 2013 (online)

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Abstract

A new and efficient synthetic approach to [gem-bis(alkylthio)vinyl]allenes has been developed involving iron(III)-catalyzed dehydration C(sp2)–C(sp2) coupling of tertiary propargyl alcohols and α-oxo ketene dithioacetals, affording a variety of [gem-bis(alkylthio)vinyl]allenes in good to excellent yields.

Key words

iron catalysis - tertiary propargyl alcohols - α-oxo ketene dithioacetals - allenic carbocation - [gem-bis(alkylthio)vinyl]allenes

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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