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Z-Selective Alkyne Functionalization Catalyzed by a trans-Dihydride N-Heterocyclic Carbene (NHC) Iron Complex.
Inorganic Chemistry ( IF 4.6 ) Pub Date : 2020-09-21 , DOI: 10.1021/acs.inorgchem.0c02057
Subhash Garhwal 1 , Natalia Fridman 1 , Graham de Ruiter 1
Affiliation  

The Z-selective functionalization of terminal alkynes is a useful transformation in organic chemistry and mainly catalyzed by noble metals. Here, we present the Z-selective hydroboration of terminal alkynes catalyzed by a stable trans-dihydride iron complex [(PCNHCP)Fe(H)2N2)] (2). Overall, the reaction occurs at room temperature and provides near quantitative yields of the Z-vinylboronate ester. Interestingly, the same catalyst could also provide the E-vinylboronate by heating the reaction mixture at slightly elevated temperatures (50 °C). If, however, the reaction is performed in the absence of HBpin, rapid Z-selective alkyne dimerization is observed, which is further discussed in this report.

中文翻译:

反式二酐N-杂环碳烯(NHC)铁络合物催化Z选择性炔烃官能化。

末端炔烃的Z选择性官能化是有机化学中的有用转变,主要由贵金属催化。在这里,我们介绍了由稳定的反式-二酐铁络合物[(PC NHC P)Fe(H)2 N 2)](2)催化的末端炔烃的Z选择性氢硼化。总的来说,该反应在室温下发生,并提供接近定量的Z-乙烯基硼酸酯。有趣的是,相同的催化剂也可以提供E-在稍微升高的温度(50°C)下加热反应混合物,生成-乙烯基硼酸酯。但是,如果该反应是在不存在HBpin的情况下进行的,则会观察到快速的Z选择性炔烃二聚化,这将在本报告中进一步讨论。
更新日期:2020-10-05
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