High Activity and Selectivity for Catalytic Alkane-Alkene Transfer (De)hydrogenation by ((PPP)-P-tBu)Ir and the Importance of Choice of a Sacrificial Hydrogen Acceptor

Gordon Benjamin M.; Parihar Ashish; Hasanayn FarajGoldman Alan S.

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High Activity and Selectivity for Catalytic Alkane-Alkene Transfer (De)hydrogenation by ((PPP)-P-tBu)Ir and the Importance of Choice of a Sacrificial Hydrogen Acceptor

机译：High Activity and Selectivity for Catalytic Alkane-Alkene Transfer (De)hydrogenation by ((PPP)-P-tBu)Ir and the Importance of Choice of a Sacrificial Hydrogen Acceptor

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The triphosphorus-coordinating pincer iridium fragment ((PPP)-P-tBu)Ir was recently reported to be highly active for the catalytic dehydrogenation of n-alkanes. Dehydrogenation is calculated to be highly regioselective for the terminal position of n-alkanes. The extremely high intermolecular selectivity observed in n-alkane/cycloalkane competition experiments supports the prediction of extremely high regioselectivity for dehydrogenation of n-alkanes. The use of sterically unhindered hydrogen acceptors is key to observing the high activity of the ((PPP)-P-tBu)Ir fragment. 4,4-Dimethylpent-1-ene (TBP) is found to be particularly convenient for this purpose. With the commonly used hydrogen acceptor 3,3-dimethylbut-1-ene (TBE), ((PPP)-P-tBu)Ir affords n-alkane dehydrogenation at a rate no different than that obtained with the well-known fragment ((PCP)-P-iPr)Ir. However, with the use of TBP as acceptor, ((PPP)-P-tBu)Ir shows much greater activity for n-alkane transfer dehydrogenation than previously reported catalysts, affording appreciable rates even at 50 degrees C, an unprecedentedly low temperature for catalytic alkane transfer dehydrogenation. Also critical to the identification of ((PPP)-P-tBu)Ir as a highly effective catalyst is the use of n-alkane substrate rather than the commonly used "model" dehydrogenation substrate, cyclooctane, with which dehydrogenation rates are much lower than those with n-alkanes.

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《Organometallics》 |2022年第22期|3426-3434|共9页
作者
Gordon Benjamin M.; Parihar Ashish; Hasanayn FarajGoldman Alan S.;
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作者单位

Amer Univ Beirut;

State Univ New Jersey;

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原文格式 PDF
正文语种英语
中图分类元素有机化合物;
关键词
IRIDIUM PINCER COMPLEXES; TRANSFER-DEHYDROGENATION; N-ALKANES; FUNCTIONALIZATION; CHEMISTRY; RHODIUM;

High Activity and Selectivity for Catalytic Alkane-Alkene Transfer (De)hydrogenation by ((PPP)-P-tBu)Ir and the Importance of Choice of a Sacrificial Hydrogen Acceptor

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