Bismuth‐ and Hafnium‐Catalyzed Hydroamination of Vinyl Arenes with Sulfonamides,Carbamates, and Carboxamides |
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| Authors: | Hongbo Qin Noriyuki Yamagiwa Dr Shigeki Matsunaga Dr Masakatsu Shibasaki Prof Dr |
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| Institution: | Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo‐ku, Tokyo 113‐0033, Japan, Fax: (+81)?3‐5684‐5206 |
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| Abstract: | Catalytic intermolecular hydroamination of vinyl arenes is described. Our initial investigation revealed that a Bi(OTf)3/Cu(CH3CN)4]PF6 system previously developed for catalytic intermolecular hydroamination of 1,3‐dienes was suitable for hydroamination of a styrene with sulfonamides, but the substrate generality of this system was unsatisfactory. Several metals were screened to expand the substrate scope, and a new Hf(OTf)4/Cu(CH3CN)4]PF6 system was determined to be highly suitable. The combination of Hf(OTf)4 and Cu(CH3CN)4]PF6 efficiently promoted the hydroamination of various vinyl arenes, including less‐reactive vinyl arenes with electron‐withdrawing groups. This strategy was applied to sulfonamides, carbamates, and carboxamides, and products were obtained in up to 99 % yield with 0.3–10 mol % catalyst loading. |
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| Keywords: | bismuth hafnium homogeneous catalysis hydroamination synthetic methods |
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