Palladium-catalyzed, direct boronic acid synthesis from aryl chlorides: a simplified route to diverse boronate ester derivatives.
Palladium-catalyzed, direct boronic acid synthesis from aryl chlorides: a simplified route to diverse boronate ester derivatives.
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钯催化的，直接的硼酸从芳基氯化物合成：一种简化的硼酸酯衍生物的途径。
DOI：
10.1021/ja1089759
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发表时间：
2010-12-22
影响因子：
15
通讯作者：
Dreher SD
中科院分区：
文献类型：
--
作者：
Molander GA;Trice SL;Dreher SD
尽管当前的许多研究集中在开发新的硼试剂和确定用于这些试剂交叉偶联的稳健催化系统，但对亲核伙伴（即硼酸和衍生物）的基本制备的研究程度较低。目前大多数获取硼酸的方法都是间接的，并且需要苛刻的条件或昂贵的试剂。据报道，使用未充分利用的试剂四羟基二硼 B2(OH)4，由相应的芳基氯直接简单有效地在钯催化下合成芳基硼酸。为了确保碳-硼键的保存，硼酸以良好至优异的产率有效转化为三氟硼酸盐衍生物，而无需使用后处理或分离。此外，中间体硼酸可以容易地转化为多种有用的硼酸盐。最后，开发了一种两步一锅法，可以在 Suzuki-Miyaura 型反应中有效偶联两种芳基氯。
Although much current research focuses on developing new boron reagents and identifying robust catalytic systems for the cross-coupling of these reagents, the fundamental preparations of the nucleophilic partners (i.e., boronic acids and derivatives) has been studied to a lesser extent. Most current methods to access boronic acids are indirect and require harsh conditions or expensive reagents. A simple and efficient palladium-catalyzed, direct synthesis of arylboronic acids from the corresponding aryl chlorides using an underutilized reagent, tetrahydroxydiboron B2(OH)4, is reported. To insure preservation of the carbon-boron bond, the boronic acids were efficiently converted to the trifluoroborate derivatives in good to excellent yields without the use of a work-up or isolation. Further, the intermediate boronic acids can be easily converted to a wide range of useful boronates. Finally, a two-step, one-pot method was developed to couple two aryl chlorides efficiently in a Suzuki-Miyaura-type reaction.
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