Rhodium-catalyzed dimerization of arylacetylenes and addition of malonates to 1,3-enynes

Katsufumi Mochizuki; Kazunori Sakai; Takuya Kochi; Fumitoshi Kakiuchi

doi:10.1055/s-0033-1338471

Rhodium-catalyzed dimerization of arylacetylenes and addition of malonates to 1,3-enynes

Katsufumi Mochizuki, Kazunori Sakai, Takuya Kochi, Fumitoshi Kakiuchi

Department of Chemistry

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

17 Citations (Scopus)

Abstract

An 8-quinolinolato rhodium catalyst was found to be effective for head-to-tail selective dimerization of arylacetylenes. Formation of substituted cyclopentene and allene derivatives via alkyne dimerization and subsequent addition of malonates was also catalyzed by the 8-quinolinolato rhodium catalyst in the presence of cesium fluoride. One-pot reaction using palladium-catalyzed alkyne dimerization in conjunction with rhodium-catalyzed addition of malonates was also possible.

Original language	English
Article number	SS-2013-C0135-ST
Pages (from-to)	2088-2092
Number of pages	5
Journal	Synthesis (Germany)
Volume	45
Issue number	15
DOIs	https://doi.org/10.1055/s-0033-1338471
Publication status	Published - 2013

Keywords

allene derivatives
aromatic terminal alkynes
cyclopentene derivatives
head-to-tail dimerization
rhodium catalyst

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1055/s-0033-1338471

Cite this

@article{e38e899e00294b12abfaebc57fb264b0,

title = "Rhodium-catalyzed dimerization of arylacetylenes and addition of malonates to 1,3-enynes",

abstract = "An 8-quinolinolato rhodium catalyst was found to be effective for head-to-tail selective dimerization of arylacetylenes. Formation of substituted cyclopentene and allene derivatives via alkyne dimerization and subsequent addition of malonates was also catalyzed by the 8-quinolinolato rhodium catalyst in the presence of cesium fluoride. One-pot reaction using palladium-catalyzed alkyne dimerization in conjunction with rhodium-catalyzed addition of malonates was also possible.",

keywords = "allene derivatives, aromatic terminal alkynes, cyclopentene derivatives, head-to-tail dimerization, rhodium catalyst",

author = "Katsufumi Mochizuki and Kazunori Sakai and Takuya Kochi and Fumitoshi Kakiuchi",

year = "2013",

doi = "10.1055/s-0033-1338471",

language = "English",

volume = "45",

pages = "2088--2092",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "15",

}

TY - JOUR

T1 - Rhodium-catalyzed dimerization of arylacetylenes and addition of malonates to 1,3-enynes

AU - Mochizuki, Katsufumi

AU - Sakai, Kazunori

AU - Kochi, Takuya

AU - Kakiuchi, Fumitoshi

PY - 2013

Y1 - 2013

N2 - An 8-quinolinolato rhodium catalyst was found to be effective for head-to-tail selective dimerization of arylacetylenes. Formation of substituted cyclopentene and allene derivatives via alkyne dimerization and subsequent addition of malonates was also catalyzed by the 8-quinolinolato rhodium catalyst in the presence of cesium fluoride. One-pot reaction using palladium-catalyzed alkyne dimerization in conjunction with rhodium-catalyzed addition of malonates was also possible.

AB - An 8-quinolinolato rhodium catalyst was found to be effective for head-to-tail selective dimerization of arylacetylenes. Formation of substituted cyclopentene and allene derivatives via alkyne dimerization and subsequent addition of malonates was also catalyzed by the 8-quinolinolato rhodium catalyst in the presence of cesium fluoride. One-pot reaction using palladium-catalyzed alkyne dimerization in conjunction with rhodium-catalyzed addition of malonates was also possible.

KW - allene derivatives

KW - aromatic terminal alkynes

KW - cyclopentene derivatives

KW - head-to-tail dimerization

KW - rhodium catalyst

UR - http://www.scopus.com/inward/record.url?scp=84880916945&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84880916945&partnerID=8YFLogxK

U2 - 10.1055/s-0033-1338471

DO - 10.1055/s-0033-1338471

M3 - Article

AN - SCOPUS:84880916945

SN - 0039-7881

VL - 45

SP - 2088

EP - 2092

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 15

M1 - SS-2013-C0135-ST

ER -

Rhodium-catalyzed dimerization of arylacetylenes and addition of malonates to 1,3-enynes

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this