[Cp*IrCl2]2 catalyzed hydroborations of alkenes using a bulky dioxaborocine |
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Authors: | Nicole M Hunter Andreas Decken Stephen A Westcott |
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Institution: | a Department of Chemistry and Biochemistry, Mount Allison University, Sackville, NB, Canada E4L 1G8 b Department of Chemistry, University of New Brunswick, Fredericton, NB, Canada E3B 5A3 c Promerus LLC, 9921 Brecksville Road, Brecksville, OH 44141-3289, USA |
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Abstract: | 4,8-Di-tert-butyl-2,10-dimethyl-12H-dibenzod,g]1,3,2]dioxaborocine (1) has been prepared in high yield by the addition of H3B·SMe2 to 6,6′-methylene(2-tert-butyl-4-methylphenol). Dioxaborocine 1 is a relatively stable solid that reacts with a variety of aliphatic alkenes in the presence of catalytic amounts of Cp*IrCl2]2 to give the terminal hydroboration products. Analogous reactions with vinylarenes, however, afford the corresponding alkenylboronate esters along with equal amounts of the hydrogenation products. Boron products have been characterized by a number of physical and analytical methods, including single-crystal X-ray diffraction studies. |
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Keywords: | Borylation Catalysis Dioxaborocine Hydroboration Iridium |
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