73475-98-6Relevant academic research and scientific papers
NHC-Iridium-Catalyzed Deoxygenative Coupling of Primary Alcohols Producing Alkanes Directly: Synergistic Hydrogenation with Sodium Formate Generated in Situ
Lu, Zeye,Zheng, Qingshu,Yang, Siqi,Qian, Chun,Shen, Yajing,Tu, Tao
, p. 10796 - 10801 (2021/09/08)
The direct conversion of alcohols into long-chain alkanes is an attractive but extremely challenging approach for biomass upgrading. Here, we describe the highly selective deoxygenative coupling of aryl ethanols with primary alcohols to produce alkanes, using a bis-N-heterocyclic carbene iridium (bis-NHC-Ir) complex as the catalyst. Up to quantitative yields and selectivity with a broad substrate scope are attained in both homo- and cross-coupling reactions. Mechanistic studies reveal that the further synergistic hydrogenation of the alkene intermediates by the formate generated in situ in the presence of bis-NHC-Ir is crucial for alkane production.
Method for preparing alkane through coupling of primary alcohol catalyzed by N-heterocyclic carbene metal compound
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Paragraph 0101-0106, (2021/08/19)
The invention belongs to the technical field of transition metal catalysis and coupling reaction of biomass alcohol, and particularly relates to a method for preparing alkane in one step through self-coupling and cross-coupling of primary alcohol catalyzed by an N-heterocyclic carbene metal compound. The invention firstly provides a catalyst, namely a homogeneous N-heterocyclic carbene metal compound, for preparing alkane through primary alcohol coupling. The method comprises the following steps: by taking primary alcohol as a reaction raw material, tert-butyl alcohol salt of alkali metal, hydroxide and other strong alkalis as alkalis, the N-heterocyclic carbene metal compound as a catalyst and tertiary alcohol, benzene analogue or long-chain alkane as a solvent, reacting at 80-200 DEG C for 4-24 hours to obtain a corresponding alkane product. Compared with the prior art, the method disclosed by the invention has the advantages that the cheap and easily available biomass alcohol can be used as the starting raw material, the use of toxic phosphine-containing ligands with poor stability is avoided, the reaction selectivity and the yield can be quantified, the operation is simple and convenient, different high-purity alkane products can be obtained only through simple post-treatment, and the method is suitable for industrial amplification and application.
Ru-Catalyzed Completely Deoxygenative Coupling of 2-Arylethanols through Base-Induced Net Decarbonylation
Manojveer, Seetharaman,Forrest, Sebastian J. K.,Johnson, Magnus T.
supporting information, p. 803 - 807 (2018/01/27)
Substituted arylethanols can be coupled by using a readily available Ru catalyst in a fully deoxygenative manner to produce hydrocarbon chains in one step. Control experiments indicate that the first deoxygenation occurs through an aldol condensation, whereas the second occurs through a base-induced net decarbonylation. This double deoxygenation enables further development in the use of alcohols as versatile and green alkylating reagents, as well as in other fields, such as deoxygenation and upgrading of overfunctionalized biomass to produce hydrocarbons.
Iridium-catalyzed reactions of ω-Arylalkanols to α,ω- Diarylalkanes
Obora, Yasushi,Anno, Yuka,Okamoto, Ryuhei,Matsu-Ura, Toyomi,Ishii, Yasutaka
supporting information; experimental part, p. 8618 - 8622 (2011/11/11)
The long and the short of it: An atom-economical route to α,ω-diarylalkanes from ω-arylalkanols was achieved by a direct one-step method, or a sequential two-step method depending on the alkyl chain length. The reaction proceeded through the formation of β-methylhydroxy- α,ω-diarylalkanes by dehydrogenation/β-alkylation, followed by dehydrogenation/decarbonylation. Copyright
FREE-RADICAL PYRIDYLETHYLATION OF ARYLALKANES
Galust'yan, G. G.,Il'yasov, E. A.,Kadyrov, Ch. Sh.
, p. 307 - 310 (2007/10/02)
2-(3-Arylpropyl)pyridines were synthesized in 30-54percent yields by the free-radical addition of toluene, o-, m-, and p-xylenes, and mesitylene to 2-vinylpyridine at 250-350 deg C.The products of rearrangement of the intermediate adduct radical with 1,3-H migration were isolated and identified.
