Regiocontrolled Synthesis of Polysubstituted Pyrroles Starting from Terminal Alkynes, Sulfonyl Azides, and Allenes

Regiocontrolled Synthesis of Polysubstituted Pyrroles Starting from Terminal Alkynes, Sulfonyl Azides, and Allenes

1-Sulfonyl-1,2,3-triazoles, readily prepared from terminal alkynes and sulfonyl azides, react with allenes in the presence of a nickel(0) catalyst to produce the corresponding isopyrroles. The initially produced isopyrroles are further converted to a wide range of polysubstituted pyrroles through do...

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Veröffentlicht in:Organic letters 2013-07, Vol.15 (13), p.3298-3301
Hauptverfasser: Miura, Tomoya, Hiraga, Kentaro, Biyajima, Tsuneaki, Nakamuro, Takayuki, Murakami, Masahiro
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Azides - chemical synthesis
Azides - chemistry
Catalysis
Cyclization
Molecular Structure
Pyrroles - chemical synthesis
Pyrroles - chemistry
Stereoisomerism
Sulfones - chemistry
Triazoles - chemical synthesis
Triazoles - chemistry
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Zusammenfassung:1-Sulfonyl-1,2,3-triazoles, readily prepared from terminal alkynes and sulfonyl azides, react with allenes in the presence of a nickel(0) catalyst to produce the corresponding isopyrroles. The initially produced isopyrroles are further converted to a wide range of polysubstituted pyrroles through double bond transposition and Alder-ene reactions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401340u