Synthesis of Substituted Furan/Pyrrole-3-carboxamides through a Tandem Nucleopalladation and Isocyanate Insertion
Access to furanyl- and pyrrolyl-3-carboxamides from readily available 3-alkyne-1,2-diols and 1-amino-3-alkyn-2-ols using isocyanate as amido surrogate is demonstrated. The approach constitutes a successful unprecedented combination of heteropalladation and isocyanate insertion, a new avenue for nove...
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Veröffentlicht in: | Organic letters 2016-09, Vol.18 (17), p.4332-4335 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | Access to furanyl- and pyrrolyl-3-carboxamides from readily available 3-alkyne-1,2-diols and 1-amino-3-alkyn-2-ols using isocyanate as amido surrogate is demonstrated. The approach constitutes a successful unprecedented combination of heteropalladation and isocyanate insertion, a new avenue for novel amide bond constructions. The mechanism likely involves a 6-membered oxaaminopalladacycle as the key intermediate. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.6b02077 |