Direct formation of functionalized ketones via the coupling of functionalized organocopper reagents with acid chlorides |
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| Affiliation: | 1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation;2. D. I. Mendeleev University of Chemical Technology of Russia, 125047 Moscow, Russian Federation;3. All-Russian Research Institute of Phytopathology, 143050 B.Vyazyomy, Moscow Region, Russian Federation;1. Novosibirsk State University, Pirogova, 2, Novosibirsk 630090, Russia;2. Heilongjiang University, Xue Fu Road, No. 74, Nan-gang, Harbin 150080, PR China;3. Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, Pr. Akademika Lavrentieva, 5, Novosibirsk 630090, Russia;1. NEUROFARBA, Sezione di Farmaceutica e Nutraceutica, Università degli Studi di Firenze, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Firenze, Italy;2. Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK;3. NEUROFARBA, Sezione di Farmacologia e Tossicologia, Università degli Studi di Firenze, Viale Pieraccini 6, 50139 Firenze, Italy;1. School of Chemical Engineering, The University of Queensland, Brisbane, Queensland 4072, Australia;3. Lambung Mangkurat University, Chemical Engineering Department, Jl. A. Yani KM 36 Banjarbaru, South Kalimantan 70714, Indonesia;4. Institute of Advanced Study, University of Warwick, Coventry CV4 7HS, United Kingdom;5. International Institute for Nanocomposites Manufacturing (IINM), WMG, University of Warwick, Coventry CV4 7AL, United Kingdom;6. Monash University, Department of Chemical Engineering, Faculty of Engineering, Clayton, Victoria 3800, Australia;7. The University of Sydney, School of Chemical and Biomolecular Engineering, New South Wales 2006, Australia;1. School of Nuclear Science and Technology, Lanzhou University, Lanzhou 730000, China;2. Engineering Research Center for Neutron Application Technology, Ministry of Education, Lanzhou University, Lanzhou 730000, China;3. Key Laboratory of Special Function Materials and Structure Design, Ministry of Education, Lanzhou University, Lanzhou 730000, China |
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| Abstract: | Highly reactive copper solutions have been prepared by the lithium naphthalide reduction of a copper(I) iodide/triphenyl-phosphine complex. These copper solutions react rapidly with functionalized alkyl halides to give organocopper reagents which have been effectively trapped with acid chlorides giving functionalized ketones in good yields. Ester, nitrile, chloride, remote epoxide, and, to some degree, ketone groups can be tolerated by this approach. |
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