Petrone David A, Kondo Masaru, Zeidan Nicolas, Lautens Mark
Department of Chemistry, University of Toronto, 80 St. George St., Toronto, M5S 3H6, Canada.
Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan.
Chemistry. 2016 Apr 11;22(16):5684-91. doi: 10.1002/chem.201600118. Epub 2016 Mar 4.
We have developed a protocol for a Pd(0)-catalyzed dearomative syn 1,2-diarylation of indoles using readily available boroxines (dehydrated boronic acids) as coupling partners. This reaction proceeds efficiently using PtBu3 as the ligand to divergently access to fused indolines while minimizing the extent of direct Suzuki coupling. The scope of the reaction is remarkably broad and all products are obtained as single diastereomers in moderate to excellent yields. We have also compiled data which parallels the steric and electronic properties of both substrate and boroxine with the propensity to undergo the desired dearomative process over direct Suzuki coupling.
我们已经开发出一种方案，用于钯（0）催化吲哚与易于获得的硼酸酯（脱水硼酸）作为偶联伙伴进行去芳构化顺式1,2 - 二芳基化反应。使用三叔丁基膦作为配体，该反应能高效进行，以不同方式得到稠合二氢吲哚，同时将直接铃木偶联的程度降至最低。该反应的适用范围非常广泛，所有产物均以单一非对映异构体形式得到，产率中等至优异。我们还整理了与底物和硼酸酯的空间和电子性质相关的数据，以及与直接铃木偶联相比发生所需去芳构化过程的倾向的数据。
