Sustainable Heck–Matsuda Reaction with Catalytic Amounts of Diazonium Salts: An Experimental and Theoretical Study |
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| Authors: | Dr Nicolas Susperregui Dr Karinne Miqueu Dr Jean‐Marc Sotiropoulos François Le Callonnec Prof Eric Fouquet Prof François‐Xavier Felpin |
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| Institution: | 1. Université de Pau et des Pays de l'Adour, UMR CNRS 5254, IPREM, 2, Avenue du Président Pierre Angot, 64053 Pau Cedex 9 (France), Fax: (+33)?559‐407‐862;2. Université de Bordeaux, UMR CNRS 5255, ISM, 351, Cours de la Libération, 33405 Talence Cedex (France);3. Université de Nantes, UFR Sciences et Techniques, UMR CNRS 6230, CEISAM, 2, rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France, Fax: (+33)?251‐125‐402 |
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| Abstract: | The palladium‐catalyzed Heck–Matsuda reaction with a catalytic amount of an in‐situ‐generated diazonium salt proceeded under mild and sustainable conditions. The reaction proceeded at room temperature, under base‐free conditions, and only generated tBuOH, H2O, and N2 as by‐products. Ortho‐substituted diazonium salts were more‐efficiently coupled to methyl acrylate than their corresponding para isomers, which required the addition of anisole as an additive. In support of these experimental data, we carried out theoretical studies to gain a deeper understanding of these reaction outcomes. |
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| Keywords: | density functional calculations Heck reaction reaction mechanisms palladium sustainable chemistry |
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