Studies of microwave-enhanced Suzuki–Miyaura vinylation of electron-rich sterically hindered substrates utilizing POTASSIUM VINYLTRIFLUOROBORATE (cas 13682-77-4)

Add time:09/07/2019    Source:sciencedirect.com

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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