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Synlett 2015; 26(04): 531-536
DOI: 10.1055/s-0034-1379606
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© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Phosphine-Free Direct C–H Arylation of Benzothiophenes and Benzofurans Involving MIDA Boronates

Zhiwei Wang
College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, P. R. of China   Fax: +86(371)67979408   eMail: wyj@zzu.edu.cn   eMail: hmm@zzu.edu.cn
,
Yabo Li
College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, P. R. of China   Fax: +86(371)67979408   eMail: wyj@zzu.edu.cn   eMail: hmm@zzu.edu.cn
,
Beiqi Yan
College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, P. R. of China   Fax: +86(371)67979408   eMail: wyj@zzu.edu.cn   eMail: hmm@zzu.edu.cn
,
Mengmeng Huang*
College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, P. R. of China   Fax: +86(371)67979408   eMail: wyj@zzu.edu.cn   eMail: hmm@zzu.edu.cn
,
Yangjie Wu*
College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, P. R. of China   Fax: +86(371)67979408   eMail: wyj@zzu.edu.cn   eMail: hmm@zzu.edu.cn
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Publikationsverlauf

Received: 30. September 2014

Accepted after revision: 27. Oktober 2014

Publikationsdatum:
09. Januar 2015 (online)

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Abstract

With high regioselectivity, a series of benzoheterocyclic compounds were synthesized via palladiium-catalyzed phosphine-free C–H arylation of benzothiophenes/benzofurans with aryl MIDA boronates at 30–50 °C in moderate to excellent yields. MIDA boronates were used in C–H arylation of heterocycles for the first time. Under the optimal conditions, the benzothiophenes could be transformed into the β-arylbenzothiophenes, and the benzofurans gave only α-aryl-substituted products.

Key words

C–H arylation - benzothiophene - benzofuran - MIDA boronate - bis(alkoxo)palladium(II) complex

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379606.
  • Supporting Information
 

  • References and Notes

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