Homometathesis and cross-metathesis coupling of phosphine-borane templates with electron-rich and electron-poor olefins |
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| Affiliation: | 1. Tarragona, Spain;2. Riverside, CA, USA;1. School of Chemistry and Chemical Engineering, School of Biological and Medical Engineering, Hefei University of Technology, PR China;2. Key Laboratory of Advanced Functional Materials and Devices, Anhui Province, Hefei 230009, PR China;3. Henry Samueli School of Engineering and Applied Sciences, University of California, Los Angeles, CA 90095-1595, USA;1. CNRS, LGC (Laboratoire de Génie Chimique), 4 Allée Emile Monso, BP 84234, 31432 Toulouse Cedex 4, France;2. CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse Cedex 4, France;3. Université de Toulouse, INPT, UPS, Toulouse, France;4. Université de Lyon, Univ. Lyon 1, CPE Lyon, CNRS, UMR 5265, C2P2 (Chemistry, Catalysis, Polymers & Processes), Team LCPP Bat 308F, 43 Bd du 11 Novembre 1918, 69616 Villeurbanne, France;5. Institut Universitaire de France, 103, bd Saint-Michel, 75005 Paris, France;1. N.N. Vorozhtsov Institute of Organic Chemistry, 9 Ac. Lavrentiev Avenue, Novosibirsk 630090, Russia;2. Novosibirsk State University, 2 Pirogova Str., Novosibirsk 630090, Russia;3. Institute of Chemical Kinetics and Combustion, 3 Institutskaya Str., 630090 Novosibirsk, Russia;4. International Tomography Center, 3a Institutskaya Str., 630090 Novosibirsk, Russia;1. Institute of Modern Physics, Fudan University, Shanghai 200433, China;2. Research Center of Laser Fusion, CAEP, Mianyang 621900, China;3. Institute of Nuclear Physics and Chemistry, CAEP, Mianyang 621900, China;1. Graduate School of Natural Science and Technology, Okayama University, Tsushima-Naka 3-1-1, Okayama 700-8530, Japan;2. Nihon Pharmaceutical University, Komuro 10281, Ina, Kitaadachi, Saitama 362-0806, Japan |
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| Abstract: | Ruthenium-catalysed olefin cross-metathesis can be used to synthesise structurally diverse acyclic phosphines protected as their borane complexes. Homodimerisations have been investigated and proved successful only for the allyl-substituted borane-protected phosphines. In the presence of various olefinic partners, allyl-substituted P templates reacted in cross-couplings to give predominantly the E products but traces of the Z isomers were always detected in the crude reaction mixtures. In contrast, cross-metathesis of vinyl-substituted phosphine boranes took place with exclusive E-selectivity. Although the conversions were consistently very good to excellent, the yields of purified products were often significantly lower suggesting that some of the newly formed compounds are prone to decompose upon purification. |
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