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Synfacts 2011(12): 1293-1293  
DOI: 10.1055/s-0031-1289400
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Two-Step Heck-Mediated Synthesis of Pyrroles from Sulfonamides and Bromoacetylenes

Contributor(s): Victor Snieckus, Yigang Zhao
M. Yamagishi, K. Nishigai, T. Hata, H. Urabe*
Tokyo Institute of Technology, Yokohama, Japan
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Publication History

Publication Date:
18 November 2011 (online)

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Significance

Reported is a two-step synthesis of 2,4-disubstituted pyrroles involving hydroamination of bromoacetylenes with sulfonamides to form (Z)-1-bromo-2-(sulfonylamino)-1-alkenes ­selectively, followed by an intramolecular Heck ­reaction-isomerization to afford pyrroles in good yields. Notably, a one-pot process for the two-step synthesis was also achieved. However, the scope and limitations of this process were not well investigated.