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Synlett 2014; 25(15): 2143-2148
DOI: 10.1055/s-0034-1378547
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of N-Benzothiazol-2-yl-amides by an Iron-Catalyzed Oxidative C(sp2)–H Functionalization

Junke Wang
a   Key Laboratory of Hexi Corridor Resources Utilization of Gansu, College of Chemistry and Chemical Engineering, Hexi University, Zhangye 734000, P. R. of China   Fax: +86(936)8282066   eMail: wangjk@hxu.edu.cn
b   Gansu Engineering Laboratory of Applied Fungus, Hexi University, Zhangye 734000, P. R. of China
,
Yingxiao Zong*
a   Key Laboratory of Hexi Corridor Resources Utilization of Gansu, College of Chemistry and Chemical Engineering, Hexi University, Zhangye 734000, P. R. of China   Fax: +86(936)8282066   eMail: wangjk@hxu.edu.cn
,
Xuexin Zhang
a   Key Laboratory of Hexi Corridor Resources Utilization of Gansu, College of Chemistry and Chemical Engineering, Hexi University, Zhangye 734000, P. R. of China   Fax: +86(936)8282066   eMail: wangjk@hxu.edu.cn
,
Yang Gao
a   Key Laboratory of Hexi Corridor Resources Utilization of Gansu, College of Chemistry and Chemical Engineering, Hexi University, Zhangye 734000, P. R. of China   Fax: +86(936)8282066   eMail: wangjk@hxu.edu.cn
,
Zhengliang Li
a   Key Laboratory of Hexi Corridor Resources Utilization of Gansu, College of Chemistry and Chemical Engineering, Hexi University, Zhangye 734000, P. R. of China   Fax: +86(936)8282066   eMail: wangjk@hxu.edu.cn
,
Guoren Yue
a   Key Laboratory of Hexi Corridor Resources Utilization of Gansu, College of Chemistry and Chemical Engineering, Hexi University, Zhangye 734000, P. R. of China   Fax: +86(936)8282066   eMail: wangjk@hxu.edu.cn
,
Zhengjun Quan
c   Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. of China
,
Xicun Wang
c   Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. of China
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Publikationsverlauf

Received: 13. Mai 2014

Accepted after revision: 29. Juni 2014

Publikationsdatum:
11. August 2014 (online)

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Abstract

Catalytic synthesis of N-benzothiazol-2-yl-amides from 1-acyl-3-(phenyl)thioureas was achieved in the presence of an iron catalyst through C(sp2)–H functionalization and C–S bond formation. Various N-benzothiazol-2-yl-amides were selectively obtained in good yields.

Key words

benzothiazole - iron catalysis - 1-acetyl-3-phenyl­thiourea - potassium persulfate - iron(III) chloride