Autotandem catalysis: Synthesis of pyrroles by gold-catalyzed cascade reaction

Hirofumi Ueda; Minami Yamaguchi; Hiroshi Kameya; Kenji Sugimoto; Hidetoshi Tokuyama

doi:10.1021/ol5024695

Autotandem catalysis: Synthesis of pyrroles by gold-catalyzed cascade reaction

Hirofumi Ueda, Minami Yamaguchi, Hiroshi Kameya, Kenji Sugimoto, Hidetoshi Tokuyama

PHA - Molecular Pharmaceutical Science

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

57 Citations (Scopus)

Abstract

A novel synthesis of substituted pyrroles by a gold(I)-catalyzed cascade reaction has been developed. The reaction proceeded with an autotandem catalysis consisting of an initial addition of gold-acetylide to an acetal moiety and was followed by gold-catalyzed 5-endo-dig cyclization and aromatization. Gold catalysts play a dual role in activating nucleophilicity or electrophilicity of terminal acetylenes by forming gold-acetylides or by π-coordination. The formal (3 + 2) annulation of two components provided a variety of substituted pyrroles in a modular fashion.

Original language	English
Pages (from-to)	4948-4951
Number of pages	4
Journal	Organic letters
Volume	16
Issue number	18
DOIs	https://doi.org/10.1021/ol5024695
Publication status	Published - 2014 Sep 19

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Autotandem catalysis: Synthesis of pyrroles by gold-catalyzed cascade reaction",

abstract = "A novel synthesis of substituted pyrroles by a gold(I)-catalyzed cascade reaction has been developed. The reaction proceeded with an autotandem catalysis consisting of an initial addition of gold-acetylide to an acetal moiety and was followed by gold-catalyzed 5-endo-dig cyclization and aromatization. Gold catalysts play a dual role in activating nucleophilicity or electrophilicity of terminal acetylenes by forming gold-acetylides or by π-coordination. The formal (3 + 2) annulation of two components provided a variety of substituted pyrroles in a modular fashion.",

author = "Hirofumi Ueda and Minami Yamaguchi and Hiroshi Kameya and Kenji Sugimoto and Hidetoshi Tokuyama",

year = "2014",

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T1 - Autotandem catalysis

T2 - Synthesis of pyrroles by gold-catalyzed cascade reaction

AU - Ueda, Hirofumi

AU - Yamaguchi, Minami

AU - Kameya, Hiroshi

AU - Sugimoto, Kenji

AU - Tokuyama, Hidetoshi

PY - 2014/9/19

Y1 - 2014/9/19

N2 - A novel synthesis of substituted pyrroles by a gold(I)-catalyzed cascade reaction has been developed. The reaction proceeded with an autotandem catalysis consisting of an initial addition of gold-acetylide to an acetal moiety and was followed by gold-catalyzed 5-endo-dig cyclization and aromatization. Gold catalysts play a dual role in activating nucleophilicity or electrophilicity of terminal acetylenes by forming gold-acetylides or by π-coordination. The formal (3 + 2) annulation of two components provided a variety of substituted pyrroles in a modular fashion.

AB - A novel synthesis of substituted pyrroles by a gold(I)-catalyzed cascade reaction has been developed. The reaction proceeded with an autotandem catalysis consisting of an initial addition of gold-acetylide to an acetal moiety and was followed by gold-catalyzed 5-endo-dig cyclization and aromatization. Gold catalysts play a dual role in activating nucleophilicity or electrophilicity of terminal acetylenes by forming gold-acetylides or by π-coordination. The formal (3 + 2) annulation of two components provided a variety of substituted pyrroles in a modular fashion.

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 18

ER -

Autotandem catalysis: Synthesis of pyrroles by gold-catalyzed cascade reaction

Abstract

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