Department of Chemistry, University of Pittsburgh , Pittsburgh, Pennsylvania 15260, United States.
Org Lett. 2017 Jul 7;19(13):3680-3683. doi: 10.1021/acs.orglett.7b01777. Epub 2017 Jun 22.
Boron-hydrogen bond insertion reactions of N-heterocyclic carbene (NHC) boranes and diazoesters can be catalyzed by NHC-boryl iodides and produce stable α-NHC-boryl esters. The conditions of the reaction resemble the previous rhodium-catalyzed transformations (only the catalyst is different); however, the mechanisms of the two reactions are probably very different. The new boryl iodide catalyzed method is adept at producing α-substituted-α-NHC-boryl esters, and this has led to a family of NHC-boryl esters with amino acid and amino-acid-like side chains.
N-杂环卡宾（NHC）硼烷和重氮基酯的硼-氢键插入反应可以被 NHC-硼基碘化物催化，生成稳定的α-NHC-硼基酯。反应条件类似于之前的铑催化转化（只是催化剂不同）；然而，两种反应的机制可能非常不同。新的硼基碘化物催化方法擅长生成α-取代的α-NHC-硼基酯，这导致了一系列具有氨基酸和类似氨基酸侧链的 NHC-硼基酯。
