Synthesis 2013; 45(15): 2088-2092
DOI: 10.1055/s-0033-1338471
special topic
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Dimerization of Arylacetylenes and Addition of Malonates­ to 1,3-Enynes

Katsufumi Mochizuki
Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan   Fax: +81(45)5661591   Email: kakiuchi@chem.keio.ac.jp
,
Kazunori Sakai
Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan   Fax: +81(45)5661591   Email: kakiuchi@chem.keio.ac.jp
,
Takuya Kochi
Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan   Fax: +81(45)5661591   Email: kakiuchi@chem.keio.ac.jp
,
Fumitoshi Kakiuchi*
Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan   Fax: +81(45)5661591   Email: kakiuchi@chem.keio.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 22 February 2013

Accepted after revision: 02 April 2013

Publication Date:
08 May 2013 (eFirst)

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.

Supporting Information

 
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