N-Heterocyclic Carbene Boryl Iodides Catalyze Insertion Reactions of N-Heterocyclic Carbene Boranes and Diazoesters
N-Heterocyclic Carbene Boryl Iodides Catalyze Insertion Reactions of N-Heterocyclic Carbene Boranes and Diazoesters
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DOI：
10.1021/acs.orglett.7b01777
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发表时间：
2017-07-07
期刊：
影响因子：
5.2
通讯作者：
Curran, Dennis P.
中科院分区：
文献类型：
--
作者：
Allen, Thomas H.;Kawamoto, Takuji;Curran, Dennis P.
N-杂环卡宾(NHC)、硼烷和重氮酯的硼氢键插入反应可以被NHC-碘化硼催化，生成稳定的α-NHC-硼酯。反应的条件类似于以前的铑催化转化(只是催化剂不同)；但是，这两个反应的机理可能是非常不同的。新的碘化硼催化方法擅长于合成α-取代-α-NHC-硼酯，这导致了一系列具有氨基酸和类氨基酸侧链的NHC-硼酯。
Boron-hydrogen bond insertion reactions of N-heterocyclic carbene (NHC) boranes and diazoesters can be catalyzed by NHC-boryl iodides and produce stable alpha-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 alpha-substituted-alpha-NHC-boryl esters, and this has led to a family of NHC-boryl esters with amino acid and amino-acid-like side chains.