Brooker Matthew D, Cooper Stefan M, Hodges Dena R, Carter Rhiannon R, Wyatt Justin K
Department of Chemistry, Trident Technical College, 7000 Rivers Ave. Charleston, SC 29455, USA.
Tetrahedron Lett. 2010 Dec 22;51(51):6748-6752. doi: 10.1016/j.tetlet.2010.10.087.
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.
在调节溶剂比例、辐照时间和催化剂负载量以寻找最佳条件的同时，利用微波辐射进行了空间位阻且富电子的邻位、邻'-取代芳基卤化物与乙烯基三氟硼酸钾的铃木-宫浦交叉偶联反应。苄基3,5-双（苄氧基）-4-溴苯甲酸酯的偶联反应生成了所需的苯乙烯衍生物和还原产物的混合物。还对4-溴-1,3,5-三甲氧基苯、4-溴-3,5-二甲氧基苯甲酸甲酯和均三甲苯溴化物进行了偶联反应，以测试该方法的适用范围。在所测试的这些底物中，只有4-溴-1,3,5-三甲氧基苯未能成功进行乙烯基化反应，据信这是由于该体系的富电子性质所致。
