Rh/Cu-cocatalyzed Ring-opening Diborylation of Dibenzothiophenes for Aromatic Metamorphosis via Diborylbiaryls
Rh/Cu-cocatalyzed Ring-opening Diborylation of Dibenzothiophenes for Aromatic Metamorphosis via Diborylbiaryls
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DOI：
10.1246/cl.170415
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发表时间：
2017-05
影响因子：
1.6
通讯作者：
Hayate Saito;K. Nogi;H. Yorimitsu
中科院分区：
文献类型：
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作者：
Hayate Saito;K. Nogi;H. Yorimitsu
在这里，我们报道了一种新的方法，通过2，2‘-二硼基联芳基将二苯并噻吩类化合物转化为其他环状骨架。在双(频那多)二硼和氟化铯的存在下，二苯并噻吩类化合物的两个C-S键发生了一系列的硼化反应，得到相应的2，2‘-二硼基联芳基化合物。作为原理证明，2，2‘-二硼基联苯被转化为一系列扩展的π-体系，如富烯、二苯并呋喃、恶草素和氮杂硼。
Here, we report a new method for aromatic metamorphosis of dibenzothiophenes into other cyclic skeletons via 2,2′-diborylbiaryls. In the presence of bis(pinacolato)diboron and cesium fluoride, the two C–S bonds of dibenzothiophenes underwent a couple of sequential borylation reactions cocatalyzed by rhodium and copper complexes to afford the corresponding 2,2′-diborylbiaryls. As a proof-of-principle, 2,2′-diborylbiphenyl was converted into a series of extended π-systems such as fulvenes, dibenzofuran, oxaborin, and azaborin.