One-Pot Carboboration of Alkynes Using Lithium Borylcyanocuprate and the Subsequent Suzuki-Miyaura Cross-Coupling of the Resulting Tetrasubstituted Alkenylborane
One-Pot Carboboration of Alkynes Using Lithium Borylcyanocuprate and the Subsequent Suzuki-Miyaura Cross-Coupling of the Resulting Tetrasubstituted Alkenylborane
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DOI：
10.1002/ejoc.201100373
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发表时间：
2011-07-01
影响因子：
2.8
通讯作者：
Nozaki, Kyoko
中科院分区：
文献类型：
--
作者：
Okuno, Yuri;Yamashita, Makoto;Nozaki, Kyoko
我们已经开发了一个一锅碳硼化内炔使用锂borylcyanocuprates 3。三中心点（thf）（3）单晶的分离使我们能够估计其结构和光谱特征。将3与酯取代的炔和炔基芳烃简单混合，然后用亲电试剂捕获所得中间体，以中等至良好的产率得到四取代的硼基烯烃4、5和8。8ba从二胺到频哪醇的配体交换允许我们探索所获得的频哪醇酯10 ba在随后的Suzuki-Miyaura交叉偶联反应中的进一步应用，以得到全碳取代的烯烃9 ba。
We have developed a one-pot carboboration of internal alkynes using lithium borylcyanocuprates 3. Isolation of single crystals of 3 center dot(thf)(3) enabled us to estimate its structural and spectroscopic features. Simple mixing of 3 with ester-substituted alkynes and alkynylarenes was followed by trapping of the resulting intermediate with electrophiles to give tetra-substituted borylalkenes 4, 5, and 8 in moderate to good yields. Ligand exchange of 8ba from diamine to pinacol allowed us to explore further application of obtained pinacol ester 10ba to subsequent Suzuki-Miyaura cross-coupling reactions to give all-carbon substituted alkene 9ba.