Arylboronic acids as versatile coupling partners in fast microwave promoted oxidative Heck chemistry |
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Authors: | Andappan Murugaiah M S Nilsson Peter Larhed Mats |
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Institution: | Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry, Biomedical Centre, Uppsala University, Uppsala, Sweden. |
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Abstract: | The useful and selective reactivity of arylboronic acids makes them favourite building blocks for many modern organic chemistry applications like the metal-mediated formation of C-C, C-O, C-N, and C-S bonds. This report describes oxidative Heck coupling reactions of arylboronic acids and olefins, which were conveniently and rapidly (5-30 min) carried out under air with temperature-controlled microwave heating. Different reaction conditions were investigated with regard to both microwave heating capability and chemical productivity. Copper(II) acetate was identified as a microwave compatible reoxidant of Pd(0). The scope and limitations of this high-speed chemistry protocol with diverse olefins and organoboronic acids are discussed. |
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