Thermal, Catalytic Conversion of Alkanes to Linear Aldehydes and Linear Amines

Journal of the American Chemical Society
Xinxin TangZheng Huang

Abstract

Alkanes, the main constituents of petroleum, are attractive feedstocks for producing value-added chemicals. Linear aldehydes and amines are two of the most important building blocks in the chemical industry. To date, there have been no effective methods for directly converting n-alkanes to linear aldehydes and linear amines. Here, we report a molecular dual-catalyst system for production of linear aldehydes via regioselective carbonylation of n-alkanes. The system is comprised of a pincer iridium catalyst for transfer-dehydrogenation of the alkane using t-butylethylene or ethylene as a hydrogen acceptor working sequentially with a rhodium catalyst for olefin isomerization-hydroformylation with syngas. The system exhibits high regioselectivity for linear aldehydes and gives high catalytic turnover numbers when using ethylene as the acceptor. In addition, the direct conversion of light alkanes, n-pentane and n-hexane, to siloxy-terminated alkyl aldehydes through a sequence of Ir/Fe-catalyzed alkane silylation and Ir/Rh-catalyzed alkane carbonylation, is described. Finally, the Ir/Rh dual-catalyst strategy has been successfully applied to regioselective alkane aminomethylation to form linear alkyl amines.

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Citations

May 2, 2019·Organic & Biomolecular Chemistry·Xue-Mei ZhaoXin-Qi Hao
Apr 10, 2020·Chemical Communications : Chem Comm·Ji YangMatthias Beller
Oct 1, 2021·Journal of the American Chemical Society·Min-Jie ZhouZheng Huang

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