C-H Borylation by Platinum Catalysis
C-H Borylation by Platinum Catalysis
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DOI：
10.1246/bcsj.20160391
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发表时间：
2017-03-01
影响因子：
4
通讯作者：
Chatani, Naoto
中科院分区：
文献类型：
--
作者：
Furukawa, Takayuki;Tobisu, Mamoru;Chatani, Naoto
在此，我们描述了铂催化的芳香族C-H键的硼基化反应。当使用双（频哪醇）二硼作为硼源时，发现N-杂环卡宾连接的铂催化剂是芳香族C（sp（2））-H键硼基化的有效催化剂。这些Pt催化剂的最显著特征是它们对经历硼化反应的C-H键周围的空间位阻程度缺乏敏感性。这些Pt催化剂允许合成空间拥挤的2，6-二取代的苯基硼酸酯，否则难以使用现有的C-H硼基化方法合成。此外，铂催化允许氟芳烃系统中氟取代基邻位的C-H键的位点选择性硼基化。初步机制的研究和工作，对这种铂催化的C-H硼化过程的合成应用进行了说明。
Herein, we describe the platinum-catalyzed borylation of aromatic C-H bonds. N-Heterocyclic carbene-ligated platinum catalysts are found to be efficient catalysts for the borylation of aromatic C(sp(2))-H bonds when bis(pinacolato)diboron is used as the boron source. The most remarkable feature of these Pt catalysts is their lack of sensitivity towards the degree of steric hindrance around the C-H bonds undergoing the borylation reaction. These Pt catalysts allow for the synthesis of sterically congested 2,6-disubstituted phenylboronic esters, which are otherwise difficult to synthesize using existing C-H borylation methods. Furthermore, platinum catalysis allows for the site-selective borylation of the C-H bonds ortho to fluorine substituents in fluoroarene systems. Preliminary mechanistic studies and work towards the synthetic application of this platinum catalyzed C-H borylation process are described.