Copper-Catalyzed Coupling Reaction of Secondary Alkyl 2-Pyridinesulfonates with Alkyl Lithium-Based Reagents |
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| Authors: | Yuta Sato Akito Osada Dr Narihito Ogawa Dr Yuichi Kobayashi |
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| Institution: | 1. Department of Applied Chemistry, Meiji University, 1-1-1, Higashimita, Tama-ku, Kawasaki, Kanagawa, 214-8571 Japan;2. Organization for the Strategic Coordination for Research and Intellectual Properties, Meiji University, 1-1-1, Higashimita, Tama-ku, Kawasaki, Kanagawa, 214-8571 Japan |
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| Abstract: | The Cu(OTf)2-catalyzed alkyl–alkyl coupling reaction of a secondary substrate MeCH(OSO2Py)CH2CH2C6H4(4-OMe) with a nBuLi-based reagent prepared by transmetalation with MgBr2 ? THF3 in THF produced a coupling product in 74 % yield. The use of soluble MgBr2 ? THF3 in THF was required for this reaction. This method was applied to sBuLi and Ph(CH2)4Li. In contrast, transmetalation of MeLi with soluble MgCl2 ? THF2 in THF produced the Me reagent, which was reactive for the coupling reaction. The reaction proceeded with inversion of the stereogenic carbon. Furthermore, (S)-14-methyloctadecan-2-one, a sex pheromone produced by lichen moths, was synthesized. |
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| Keywords: | C?C coupling copper Lichen Moth pheromone alkyl lithium pyridinesulfonates |
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