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Synthesis 2014; 46(15): 2051-2056
DOI: 10.1055/s-0033-1341265
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Dihydropyrrole Derivatives by a Palladium-Catalyzed Heck and Suzuki Cross-Coupling Cascade Reaction

Jinsong Peng*
a   Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin, 150040, P. R. of China   Fax: +86(451)82190679   eMail: jspeng1998@nefu.edu.cn   eMail: 080122@nefu.edu.cn
b   Post-Doctoral Mobile Research Station of Forestry Engineering, Northeast Forestry University, Harbin, 150040, P. R. of China
,
Yan Zhao
a   Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin, 150040, P. R. of China   Fax: +86(451)82190679   eMail: jspeng1998@nefu.edu.cn   eMail: 080122@nefu.edu.cn
,
Jingjie Zhou
a   Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin, 150040, P. R. of China   Fax: +86(451)82190679   eMail: jspeng1998@nefu.edu.cn   eMail: 080122@nefu.edu.cn
,
Yuehang Ding
a   Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin, 150040, P. R. of China   Fax: +86(451)82190679   eMail: jspeng1998@nefu.edu.cn   eMail: 080122@nefu.edu.cn
,
Chunxia Chen*
a   Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin, 150040, P. R. of China   Fax: +86(451)82190679   eMail: jspeng1998@nefu.edu.cn   eMail: 080122@nefu.edu.cn
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Publikationsverlauf

Received: 16. Januar 2014

Accepted after revision: 31. März 2014

Publikationsdatum:
13. Mai 2014 (online)

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Abstract

An expedient protocol for the synthesis of 5-aryl-2,3-dihydropyrroles, starting from N-tosyl-protected 2-methylprop-2-en-1-amine, alkynyl bromides, and arylboronic acids, is described. The sequential reaction sequence involves nucleophilic addition of the sulfonamide to the alkynyl bromide, followed by a palladium-catalyzed tandem intramolecular Heck and intermolecular Suzuki cross-coupling reaction of the bromoalkene adduct.

Key words

pyrroles - palladium - catalysis - tandem reactions - Heck reaction - Suzuki reaction

Supporting Information

    for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
  • Supporting Information
 

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