Hydroboration of Nitriles,Esters, and Carbonates Catalyzed by Simple Earth-Abundant Metal Triflate Salts |
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Authors: | Dr Ranjeesh Thenarukandiyil Dr Vanaparthi Satheesh Dr Linda J W Shimon Dr Graham de Ruiter |
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Institution: | 1. Schulich Faculty of Chemistry, Technion – Israel Institute of Technology, Technion City, 3200008 Haifa, Israel;2. Department of Chemical Research Support, Weizmann Institute of Science, Rehovot, 7610001 Israel |
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Abstract: | During the past decade earth-abundant metals have become increasingly important in homogeneous catalysis. One of the reactions in which earth-abundant metals have found important applications is the hydroboration of unsaturated C?C and C?X bonds (X=O or N). Within these set of transformations, the hydroboration of challenging substrates such as nitriles, carbonates and esters still remain difficult and often relies on elaborate ligand designs and highly reactive catalysts (e. g., metal alkyls/hydrides). Here we report an effective methodology for the hydroboration of challenging C≡N and C=O bonds that is simple and applicable to a wide set of substrates. The methodology is based on using a manganese(II) triflate salt that, in combination with commercially available potassium tert-butoxide and pinacolborane, catalyzes the hydroboration of nitriles, carbonates, and esters at room temperature and with near quantitative yields in less than three hours. Additional studies demonstrated that other earth-abundant metal triflate salts can facilitate this reaction as well, which is further discussed in this report. |
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Keywords: | Earth-Abundant Metals Hydroboration Manganese Nitriles Carbonates and Esters |
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