Iron-Catalyzed Alkyl–Alkyl Suzuki–Miyaura Coupling†
Dr. Takuji Hatakeyama
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
PRESTO (Japan) Science and Technology Agency (Japan)
Search for more papers by this authorToru Hashimoto
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorDr. Kalum K. A. D. S. Kathriarachchi
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorTakeshi Zenmyo
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorDr. Hirofumi Seike
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Masaharu Nakamura
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)Search for more papers by this authorDr. Takuji Hatakeyama
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
PRESTO (Japan) Science and Technology Agency (Japan)
Search for more papers by this authorToru Hashimoto
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorDr. Kalum K. A. D. S. Kathriarachchi
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorTakeshi Zenmyo
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorDr. Hirofumi Seike
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Masaharu Nakamura
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)Search for more papers by this authorThis work was funded by the Japan Society for the Promotion of Science (JSPS) through the “Funding Program for Next Generation World-Leading Researchers (NEXT Program),” initiated by the Council for Science and Technology Policy (CSTP). Financial support from Tosoh Finechem Corporation is also acknowledged. The synchrotron X-ray absorption measurement was performed at the BL14B2 in the SPring-8 with the approval of JASRI (2009A1848, 2009B1783, 2011B1945, 2012A1595). M.N. thanks Prof. K. Fukase and Dr. Y. Fujimoto for valuable discussion on the coupling reaction with long-chain alkyl substrates.
Graphical Abstract
Chemoselective Suzuki–Miyaura coupling of primary and secondary alkyl halides is realized by using an iron/Xantphos catalyst. Primary and secondary alkyl bromides undergo the reaction to give the coupling products in good yields. Application to the synthesis of long-chain fatty acid derivatives is also described (see scheme).
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
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