School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan).
Angew Chem Int Ed Engl. 2014 Nov 24;53(48):13150-4. doi: 10.1002/anie.201408345. Epub 2014 Oct 24.
Arynes were generated in situ from ortho-silyl aryl triflates and fluoride ions in the presence of stable N-heterocyclic carbene boranes (NHC-BH3). Spontaneous hydroboration ensued to provide stable B-aryl-substituted NHC-boranes (NHC-BH2Ar). The reaction shows good scope in terms of both the NHC-borane and aryne components and provides direct access to mono- and disubstituted NHC-boranes. The formation of unusual ortho regioisomers in the hydroboration of arynes with an electron-withdrawing group supports a hydroboration process with hydride-transfer character.
芳基硅醚在稳定的 N-杂环卡宾硼烷（NHC-BH3）存在下原位生成芳炔，随后发生自发的硼氢化反应，得到稳定的 B-芳基取代的 NHC-硼烷（NHC-BH2Ar）。该反应在 NHC-硼烷和芳炔两部分均具有良好的适用范围，可直接得到单取代和二取代的 NHC-硼烷。带有吸电子基团的芳炔硼氢化反应形成了不常见的邻位区域异构体，支持了具有氢化物转移特征的硼氢化反应过程。
