Regiocontrolled synthesis of polysubstituted pyrroles starting from terminal alkynes, sulfonyl azides, and allenes

Tomoya Miura; Kentaro Hiraga; Tsuneaki Biyajima; Takayuki Nakamuro; Masahiro Murakami

doi:10.1021/ol401340u

Regiocontrolled synthesis of polysubstituted pyrroles starting from terminal alkynes, sulfonyl azides, and allenes

Tomoya Miura, Kentaro Hiraga, Tsuneaki Biyajima, Takayuki Nakamuro, Masahiro Murakami

Research output: Contribution to journal › Article › peer-review

127 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	3298-3301
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	13
DOIs	https://doi.org/10.1021/ol401340u
Publication status	Published - Jul 5 2013
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol401340u

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abstract = "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.",

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AU - Miura, Tomoya

AU - Hiraga, Kentaro

AU - Biyajima, Tsuneaki

AU - Nakamuro, Takayuki

AU - Murakami, Masahiro

PY - 2013/7/5

Y1 - 2013/7/5

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AB - 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.

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Regiocontrolled synthesis of polysubstituted pyrroles starting from terminal alkynes, sulfonyl azides, and allenes

Abstract

ASJC Scopus subject areas

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