Studies of microwave-enhanced Suzuki-Miyaura vinylation of electron-rich sterically hindered substrates utilizing potassium vinyltrifluoroborate |
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Authors: | Brooker Matthew D Cooper Stefan M Hodges Dena R Carter Rhiannon R Wyatt Justin K |
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Institution: | a Department of Chemistry, Trident Technical College, 7000 Rivers Ave. Charleston, SC 29455, USA b Department of Chemistry and Biochemistry, College of Charleston, 66 George St., Charleston, SC 29424, USA |
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Abstract: | The Suzuki-Miyaura cross-coupling of sterically hindered and electron-rich ortho,ortho′-substituted aryl halides with potassium vinyltrifluoroborate utilizing microwave irradiation has been conducted while adjusting solvent ratio, irradiation time, and catalyst loading to find optimal conditions. Coupling of benzyl 3,5-bis(benzyloxy)-4-bromobenzoate leads to a mixture of the desired styrene derivative and the reduced product. 4-Bromo-1,3,5-trimethoxybenzene, methyl 4-bromo-3,5-dimethoxybenzoate, and mesitylene bromide were also coupled to test the breadth and scope of this methodology. Of these substrates tested only 4-bromo-1,3,5-trimethoxybenzene was not vinylated successfully, which is believed to be due to the electron-rich nature of this system. |
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Keywords: | Suzuki-Miyaura Potassium vinyltrifluoroborate Styrenes Palladium catalysis Hindered aryl bromides |
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