Ruthenium-catalyzed addition of olefinic C-H bonds in conjugate enones to acetylenes to give conjugate dienones

Fumitoshi Kakiuchi, Tomohiro Uetsuhara, Yasuo Tanaka, Naoto Chatani, Shinji Murai

Research output: Contribution to journalArticle

65 Citations (Scopus)

Abstract

Addition of a β C-H bond in conjugate enones to internal acetylenes to give conjugate dienones proceeded with the aid of RuH2(CO)(PPh3)3 as the catalyst. The reaction of pivaloylcyclohexene with diphenylacetylene gave the corresponding dienone in high yield. Acylpyranes can also be used in these olefinic C-H/acetylene coupling reactions. Phenyltrimethylsilylacetylene is also able to serve as a C-H bond acceptor.

Original languageEnglish
Pages (from-to)511-514
Number of pages4
JournalJournal of Molecular Catalysis A: Chemical
Volume182-183
DOIs
Publication statusPublished - 2002 May 31
Externally publishedYes

Fingerprint

Acetylene
Alkynes
Ruthenium
Carbon Monoxide
acetylene
ruthenium
Catalysts
catalysts
biphenylacetylene

Keywords

  • C-H bond
  • Conjugate dienones
  • Conjugate enones
  • Olefinic C-H/acetylene coupling
  • Ruthenium catalyst

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology

Cite this

Ruthenium-catalyzed addition of olefinic C-H bonds in conjugate enones to acetylenes to give conjugate dienones. / Kakiuchi, Fumitoshi; Uetsuhara, Tomohiro; Tanaka, Yasuo; Chatani, Naoto; Murai, Shinji.

In: Journal of Molecular Catalysis A: Chemical, Vol. 182-183, 31.05.2002, p. 511-514.

Research output: Contribution to journalArticle

Kakiuchi, Fumitoshi ; Uetsuhara, Tomohiro ; Tanaka, Yasuo ; Chatani, Naoto ; Murai, Shinji. / Ruthenium-catalyzed addition of olefinic C-H bonds in conjugate enones to acetylenes to give conjugate dienones. In: Journal of Molecular Catalysis A: Chemical. 2002 ; Vol. 182-183. pp. 511-514.
@article{cedc2fd1cde64f84a055be0945684dbc,
title = "Ruthenium-catalyzed addition of olefinic C-H bonds in conjugate enones to acetylenes to give conjugate dienones",
abstract = "Addition of a β C-H bond in conjugate enones to internal acetylenes to give conjugate dienones proceeded with the aid of RuH2(CO)(PPh3)3 as the catalyst. The reaction of pivaloylcyclohexene with diphenylacetylene gave the corresponding dienone in high yield. Acylpyranes can also be used in these olefinic C-H/acetylene coupling reactions. Phenyltrimethylsilylacetylene is also able to serve as a C-H bond acceptor.",
keywords = "C-H bond, Conjugate dienones, Conjugate enones, Olefinic C-H/acetylene coupling, Ruthenium catalyst",
author = "Fumitoshi Kakiuchi and Tomohiro Uetsuhara and Yasuo Tanaka and Naoto Chatani and Shinji Murai",
year = "2002",
month = "5",
day = "31",
doi = "10.1016/S1381-1169(01)00500-3",
language = "English",
volume = "182-183",
pages = "511--514",
journal = "Journal of Molecular Catalysis A: Chemical",
issn = "1381-1169",
publisher = "Elsevier",

}

TY - JOUR

T1 - Ruthenium-catalyzed addition of olefinic C-H bonds in conjugate enones to acetylenes to give conjugate dienones

AU - Kakiuchi, Fumitoshi

AU - Uetsuhara, Tomohiro

AU - Tanaka, Yasuo

AU - Chatani, Naoto

AU - Murai, Shinji

PY - 2002/5/31

Y1 - 2002/5/31

N2 - Addition of a β C-H bond in conjugate enones to internal acetylenes to give conjugate dienones proceeded with the aid of RuH2(CO)(PPh3)3 as the catalyst. The reaction of pivaloylcyclohexene with diphenylacetylene gave the corresponding dienone in high yield. Acylpyranes can also be used in these olefinic C-H/acetylene coupling reactions. Phenyltrimethylsilylacetylene is also able to serve as a C-H bond acceptor.

AB - Addition of a β C-H bond in conjugate enones to internal acetylenes to give conjugate dienones proceeded with the aid of RuH2(CO)(PPh3)3 as the catalyst. The reaction of pivaloylcyclohexene with diphenylacetylene gave the corresponding dienone in high yield. Acylpyranes can also be used in these olefinic C-H/acetylene coupling reactions. Phenyltrimethylsilylacetylene is also able to serve as a C-H bond acceptor.

KW - C-H bond

KW - Conjugate dienones

KW - Conjugate enones

KW - Olefinic C-H/acetylene coupling

KW - Ruthenium catalyst

UR - http://www.scopus.com/inward/record.url?scp=0037205145&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037205145&partnerID=8YFLogxK

U2 - 10.1016/S1381-1169(01)00500-3

DO - 10.1016/S1381-1169(01)00500-3

M3 - Article

AN - SCOPUS:0037205145

VL - 182-183

SP - 511

EP - 514

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

SN - 1381-1169

ER -