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Ligand-Controlled Copper(I)-Catalyzed Cross-Coupling of Secondary and Primary Alcohols to α-Alkylated Ketones, Pyridines, and Quinolines
Organic Letters ( IF 5.2 ) Pub Date : 2018-01-16 00:00:00 , DOI: 10.1021/acs.orglett.7b03726
Da-Wei Tan 1 , Hong-Xi Li 1, 2 , Da-Liang Zhu 1 , Hai-Yan Li 1 , David James Young 3 , Jian-Lin Yao 1 , Jian-Ping Lang 1, 2
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One hexanuclear Cu(I) cluster of 4,6-dimethylpyrimidine-2-thiolate efficiently catalyzes the dehydrogenative cross-coupling of secondary and primary alcohols to α-alkylated ketones with high selectivity. This transformation proceeds through a one-pot sequence of dehydrogenation of alcohols, condensation of aldehydes and ketones, hydrogenation of the resulting α,β-unsaturated ketones, and dehydrogenation of the α-alkylated alcohols to generate α-alkylated ketones. This catalytic system also displays high activity for the annulation reaction of secondary alcohols with γ-amino- and 2-aminobenzyl alcohols to yield pyridines and quinolines, respectively.

中文翻译:

配体控制的铜(I)催化的仲醇和伯醇与α-烷基化酮,吡啶和喹啉的交叉偶联

一个4,6-二甲基嘧啶-2-硫醇盐的六核Cu(I)簇可以高选择性地催化仲醇和伯醇与α-烷基化酮的脱氢交叉偶联。通过一锅法进行醇的脱氢,醛和酮的缩合,所得的α,β-不饱和酮的氢化以及α-烷基化的醇的脱氢以生成α-烷基化的酮的顺序进行。该催化体系对于仲醇与γ-氨基和2-氨基苄醇的环化反应也分别显示出较高的活性,以分别产生吡啶和喹啉。
更新日期:2018-01-16
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