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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 941-951

http://dx.doi.org/10.1351/pac200880050941

Carbon-carbon bond-forming reactions using alkyl fluorides

Jun Terao, Hirohisa Todo, Hiroyasu Watabe, Aki Ikumi, Yoshiaki Shinohara and Nobuaki Kambe

Department of Applied Chemistry and Center for Atomic and Molecular Technologies, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan

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  • Iwasaki Takanori, Higashikawa Kiyokazu, Reddy Vutukuri P., Ho Willbe W. S., Fujimoto Yukari, Fukase Koichi, Terao Jun, Kuniyasu Hitoshi, Kambe Nobuaki: NickelButadiene Catalytic System for the Cross-Coupling of Bromoalkanoic Acids with Alkyl Grignard Reagents: A Practical and Versatile Method for Preparing Fatty Acids. Chem. Eur. J. 2013, 19, 2956. <http://dx.doi.org/10.1002/chem.201204222>
  • Mongin Florence, Harrison-Marchand Anne: Mixed AggregAte (MAA): A Single Concept for All Dipolar Organometallic Aggregates. 2. Syntheses and Reactivities of Homo/HeteroMAAs. Chem. Rev. 2013, 113, 7563. <http://dx.doi.org/10.1021/cr3002966>
  • Iwasaki Takanori, Takagawa Hiroaki, Singh Surya P., Kuniyasu Hitoshi, Kambe Nobuaki: Co-Catalyzed Cross-Coupling of Alkyl Halides with Tertiary Alkyl Grignard Reagents Using a 1,3-Butadiene Additive. J. Am. Chem. Soc. 2013, 135, 9604. <http://dx.doi.org/10.1021/ja404285b>
  • Zhan Jin-Hui, Lv Hongbin, Yu Yi, Zhang Jun-Long: Catalytic C-F Bond Activation of Perfluoroarenes by Tricoordinated Gold(I) Complexes. Adv. Synth. Catal. 2012, 354, 1529. <http://dx.doi.org/10.1002/adsc.201100843>
  • Mo Zhenbo, Zhang Qiang, Deng Liang: Dinuclear Iron Complex-Catalyzed Cross-Coupling of Primary Alkyl Fluorides with Aryl Grignard Reagents. Organometallics 2012, 31, 6518. <http://dx.doi.org/10.1021/om300722g>
  • Mankad Neal P., Toste F. Dean: C(sp3)–F reductive elimination from alkylgold(iii) fluoride complexes. Chem Sci 2012, 3, 72. <http://dx.doi.org/10.1039/c1sc00515d>
  • Shen Ruwei, Iwasaki Takanori, Terao Jun, Kambe Nobuaki: Copper-catalyzed coupling reaction of unactivated secondary alkyl iodides with alkyl Grignard reagents in the presence of 1,3-butadiene as an effective additive. Chem. Commun. 2012, 48, 9313. <http://dx.doi.org/10.1039/c2cc34847k>
  • Flückiger Michelle, Togni Antonio: Iron(II)-Catalyzed Asymmetric Hydrosilylation of Acetophenone. Eur J Org Chem 2011, 2011, 4353. <http://dx.doi.org/10.1002/ejoc.201100550>
  • Yanai Hikaru, Okada Haruna, Sato Azusa, Okada Midori, Taguchi Takeo: Copper-free defluorinative alkylation of allylic difluorides through Lewis acid-mediated C–F bond activation. Tetrahedron Letters 2011, 52, 2997. <http://dx.doi.org/10.1016/j.tetlet.2011.03.148>
  • Kambe Nobuaki, Terao Jun, Iwasaki Takanori: Transition Metal Catalyzed Alkylation at sp3-, sp2-, and sp-Carbons. J Syn Org Chem Jpn 2011, 69, 1271. <http://dx.doi.org/10.5059/yukigoseikyokaishi.69.1271>
  • Aoyama Motoshi, Hara Shoji: Synthesis of functionalized adamantanes from fluoroadamantanes. Tetrahedron 2009, 65, 3682. <http://dx.doi.org/10.1016/j.tet.2009.02.059>
  • Terao Jun, Nakamura Misaki, Kambe Nobuaki: Non-catalytic conversion of C–F bonds of benzotrifluorides to C–C bonds using organoaluminium reagents. Chem Commun 2009, 6011. <http://dx.doi.org/10.1039/b915620h>
  • Terao Jun, Todo Hirohisa, Watabe Hiroyasu, Ikumi Aki, Shinohara Yoshiaki, Kambe Nobuaki: ChemInform Abstract: Carbon-Carbon Bond-Forming Reactions Using Alkyl Fluorides. ChemInform 2008, 39. <http://dx.doi.org/10.1002/chin.200843247>