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Asian Journal of Organic Chemistry · 2023 ·Vol. 12 ·期 5 ·e202300015 · IF 2.7

Transition-Metal-Free α-C-Alkylation of Oxindoles with Alcohols

Yu-Tong Duan,Zhong-Xia Wang

Graphical Transition-metal-free reaction of oxindoles with primary or secondary alcohols in the presence of LiO t Bu affords α-C-alkylated oxindoles. Transition-metal-free α-C-alkylation of oxindoles with alcohols was performed. The reaction requires the presence of LiO t Bu and proceeds under thermal conditions. The method exhibits a wide scope of substrates. Both primary and secondary aliphatic and aromatic alcohols can be employed as the alkylating reagents. Oxindole and various 1-alkyl- or 1-aryl-substituted oxindoles can be alkylated. The mechanistic studies show that the reaction may involve both free radical and aldol condensation/MPV processes.

CAS / MDL: 64-17-5 61-70-1 59-48-3

研究领域: 有机化学 · 合成化学

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Nature Communications · 2024 ·Vol. 15 ·期 1 ·1-15 · IF 14.7

Enable biomass-derived alcohols mediated alkylation and transfer hydrogenation

Liu Xixi,Huang Liang,Ma Yuandie,She Guoqiang,Zhou Peng,Zhu Liangfang,Zhang Zehui

A single-atom catalyst with generally regarded inert Zn–N 4 motifs derived from ZIF-8 is unexpectedly efficient for the activation of alcohols, enabling alcohol-mediated alkylation and transfer hydrogenation. C-alkylation of nitriles, ketones, alcohols, N -heterocycles, amides, keto acids, and esters, and N -alkylation of amines and amides all go smoothly with the developed method. Taking the α-alkylation of nitriles with alcohols as an example, the α-alkylation starts from the (1) nitrogen-doped carbon support catalyzed dehydrogenation of alcohols into aldehydes, which further condensed with nitriles to give vinyl nitriles, followed by (2) transfer hydrogenation of C=C bonds in vinyl nitriles on Zn–N 4 sites. The experimental results and DFT calculations reveal that the Lewis acidic Zn-N 4 sites promote step (2) by activating the alcohols. This is the first example of highly efficient single-atom catalysts for various organic transformations with biomass-derived alcohols as the alkylating reagents and hydrogen donors.

研究领域: 催化 · 有机化学 · 材料科学 · 化学工程

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Transition-Metal-Free α-C-Alkylation of Oxindoles with Alcohols

Enable biomass-derived alcohols mediated alkylation and transfer hydrogenation