Rhodium(III)-Catalyzed Tandem [2+2+2] Annulation–Lactamization of Anilides with Two Alkynoates via Cleavage of Two Adjacent C−H or C−H/C−O bonds

Miho Fukui; Yu Shibata; Yuki Hoshino; Haruki Sugiyama; Kota Teraoka; Hidehiro Uekusa; Keiichi Noguchi; Ken Tanaka

doi:10.1002/asia.201600943

Rhodium(III)-Catalyzed Tandem [2+2+2] Annulation–Lactamization of Anilides with Two Alkynoates via Cleavage of Two Adjacent C−H or C−H/C−O bonds

Miho Fukui, Yu Shibata, Yuki Hoshino, Haruki Sugiyama, Kota Teraoka, Hidehiro Uekusa, Keiichi Noguchi, Ken Tanaka

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

27 Citations (Scopus)

Abstract

An electron-deficient Cp^E rhodium(III) complex bearing a cyclopentadienyl ligand with two ethyl ester substituents catalyzes the tandem [2+2+2] annulation–lactamization of acetanilides with two alkynoates via cleavage of adjacent two C−H bonds to give densely substituted benzo[cd]indolones. The reactions of meta-methoxy-substituted acetanilides with two alkynoates also provided benzo[cd]indolones via cleavage of adjacent C−H/C−O bonds. Furthermore, 3,5-dimethoxyacetanilides reacted with two alkynoates to give dearomatized spiro compounds.

Original language	English
Pages (from-to)	2260-2264
Number of pages	5
Journal	Chemistry - An Asian Journal
Volume	11
Issue number	16
DOIs	https://doi.org/10.1002/asia.201600943
Publication status	Published - 2016 Aug 19
Externally published	Yes

Keywords

alkynes
anilides
annulation
benzo[cd]indolones
rhodium

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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title = "Rhodium(III)-Catalyzed Tandem [2+2+2] Annulation–Lactamization of Anilides with Two Alkynoates via Cleavage of Two Adjacent C−H or C−H/C−O bonds",

abstract = "An electron-deficient CpE rhodium(III) complex bearing a cyclopentadienyl ligand with two ethyl ester substituents catalyzes the tandem [2+2+2] annulation–lactamization of acetanilides with two alkynoates via cleavage of adjacent two C−H bonds to give densely substituted benzo[cd]indolones. The reactions of meta-methoxy-substituted acetanilides with two alkynoates also provided benzo[cd]indolones via cleavage of adjacent C−H/C−O bonds. Furthermore, 3,5-dimethoxyacetanilides reacted with two alkynoates to give dearomatized spiro compounds.",

keywords = "alkynes, anilides, annulation, benzo[cd]indolones, rhodium",

author = "Miho Fukui and Yu Shibata and Yuki Hoshino and Haruki Sugiyama and Kota Teraoka and Hidehiro Uekusa and Keiichi Noguchi and Ken Tanaka",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

month = aug,

day = "19",

doi = "10.1002/asia.201600943",

language = "English",

volume = "11",

pages = "2260--2264",

journal = "Chemistry - An Asian Journal",

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T1 - Rhodium(III)-Catalyzed Tandem [2+2+2] Annulation–Lactamization of Anilides with Two Alkynoates via Cleavage of Two Adjacent C−H or C−H/C−O bonds

AU - Fukui, Miho

AU - Shibata, Yu

AU - Hoshino, Yuki

AU - Sugiyama, Haruki

AU - Teraoka, Kota

AU - Uekusa, Hidehiro

AU - Noguchi, Keiichi

AU - Tanaka, Ken

PY - 2016/8/19

Y1 - 2016/8/19

N2 - An electron-deficient CpE rhodium(III) complex bearing a cyclopentadienyl ligand with two ethyl ester substituents catalyzes the tandem [2+2+2] annulation–lactamization of acetanilides with two alkynoates via cleavage of adjacent two C−H bonds to give densely substituted benzo[cd]indolones. The reactions of meta-methoxy-substituted acetanilides with two alkynoates also provided benzo[cd]indolones via cleavage of adjacent C−H/C−O bonds. Furthermore, 3,5-dimethoxyacetanilides reacted with two alkynoates to give dearomatized spiro compounds.

AB - An electron-deficient CpE rhodium(III) complex bearing a cyclopentadienyl ligand with two ethyl ester substituents catalyzes the tandem [2+2+2] annulation–lactamization of acetanilides with two alkynoates via cleavage of adjacent two C−H bonds to give densely substituted benzo[cd]indolones. The reactions of meta-methoxy-substituted acetanilides with two alkynoates also provided benzo[cd]indolones via cleavage of adjacent C−H/C−O bonds. Furthermore, 3,5-dimethoxyacetanilides reacted with two alkynoates to give dearomatized spiro compounds.

KW - alkynes

KW - anilides

KW - annulation

KW - benzo[cd]indolones

KW - rhodium

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U2 - 10.1002/asia.201600943

DO - 10.1002/asia.201600943

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JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

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ER -

Rhodium(III)-Catalyzed Tandem [2+2+2] Annulation–Lactamization of Anilides with Two Alkynoates via Cleavage of Two Adjacent C−H or C−H/C−O bonds

Abstract

Keywords

ASJC Scopus subject areas

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