FeCl3·6H2O-Catalyzed Synthesis of β-Ketothioesters from Chain α-Oxo Ketene Dithioactals

doi:10.1007/s40242-017-7082-1

Chemical Research in Chinese Universities ›› 2017, Vol. 33 ›› Issue (5): 746-752.doi: 10.1007/s40242-017-7082-1

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FeCl₃·6H₂O-Catalyzed Synthesis of β-Ketothioesters from Chain α-Oxo Ketene Dithioactals

ZHAO Hui¹, DIAO Quanping¹, YU Haifeng^1,2, LI Tiechun¹, LIAO Peiqiu², HOU Dongyan¹

1. School of Chemistry and Life Science, Anshan Normal University, Anshan 114007, P. R. China;
2. Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. China

Received:2017-03-07 Revised:2017-04-05 Online:2017-10-01 Published:2017-07-21
Contact: YU Haifeng,E-mail:yuhf68105@sina.com;HOU Dongyan,houdyas@163.com E-mail:yuhf68105@sina.com;houdyas@163.com
Supported by:
Supported by the Fundamental Research Funds for the Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, China(No.130028652)； the Natural Science Foundation of Liaoning Province, China(No.201602002)； the Foundation of Liaoning Province Education Administration, China(No.L2015003)； the National Natural Science Foundation of China(No.20902010).

Abstract

Abstract:

A FeCl₃·6H₂O-catalyzed synthesis of β-ketothioesters from the hydrolysis reaction of chain α-oxoketene dithioacetals was carried out. Subsequently, we explored the FeCl₃·6H₂O-catalyzed Friedel-Crafts alkylation of the synthesized β-ketothioesters with alcohols in CH₃CN at 25℃, affording the desired α-alkylated β-ketothioesters in excellent yields. Wide scope of the substrates, use of inexpensive reagents, high yields under mild reaction conditions are notable features of these reactions.

Key words: Iron(Ⅲ) chloride, Thioester, Ketene dithioacetal, Hydrolysis, Friedel-Crafts alkylation

ZHAO Hui, DIAO Quanping, YU Haifeng, LI Tiechun, LIAO Peiqiu, HOU Dongyan. FeCl₃·6H₂O-Catalyzed Synthesis of β-Ketothioesters from Chain α-Oxo Ketene Dithioactals[J]. Chemical Research in Chinese Universities, 2017, 33(5): 746-752.

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FeCl₃·6H₂O-Catalyzed Synthesis of β-Ketothioesters from Chain α-Oxo Ketene Dithioactals

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