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 journalArticle

12 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2260-2264
Number of pages5
JournalChemistry - An Asian Journal
Volume11
Issue number16
DOIs
Publication statusPublished - 2016 Aug 19
Externally publishedYes

Fingerprint

Acetanilides
Anilides
Rhodium
Carbon Monoxide
Spiro Compounds
Bearings (structural)
Esters
Electrons
Ligands

Keywords

  • alkynes
  • anilides
  • annulation
  • benzo[cd]indolones
  • rhodium

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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

In: Chemistry - An Asian Journal, Vol. 11, No. 16, 19.08.2016, p. 2260-2264.

Research output: Contribution to journalArticle

Fukui, Miho ; Shibata, Yu ; Hoshino, Yuki ; Sugiyama, Haruki ; Teraoka, Kota ; Uekusa, Hidehiro ; Noguchi, Keiichi ; Tanaka, Ken. / 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. In: Chemistry - An Asian Journal. 2016 ; Vol. 11, No. 16. pp. 2260-2264.
@article{9d2fc28f4d4846b7a67b7c238fa7acbf,
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",
year = "2016",
month = "8",
day = "19",
doi = "10.1002/asia.201600943",
language = "English",
volume = "11",
pages = "2260--2264",
journal = "Chemistry - An Asian Journal",
issn = "1861-4728",
publisher = "John Wiley and Sons Ltd",
number = "16",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=84983371771&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84983371771&partnerID=8YFLogxK

U2 - 10.1002/asia.201600943

DO - 10.1002/asia.201600943

M3 - Article

VL - 11

SP - 2260

EP - 2264

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

SN - 1861-4728

IS - 16

ER -